5.5 Fisher Projection 5.5 费舍尔投影
For the discussions so far, the perspective formula with solid and dashed wedges has been used to represent the 3D arrangement of groups bonded to a chirality center. In addition, there is another broadly applied formula for that purpose: the Fisher projection. A Fisher projection is a shortcut for showing the spatial group arrangement of a chirality center; it is easier to draw and recognize and is particularly useful for showing structures with more than one chirality center.
对于到目前为止的讨论,具有实线和虚线楔形的透视公式已用于表示键合到手性中心的基团的 3D 排列。此外,还有另一个广泛应用的公式用于此目的:费舍尔投影。费舍尔投影是显示手性中心空间群排列的捷径;它更容易绘制和识别,对于显示具有多个手性中心的结构特别有用。
In a Fisher projection, the chirality center is shown as the intersection of two perpendicular lines. The horizontal lines represent the bonds point out of the plane, and the vertical lines represent the bonds that point behind the plane.
在费舍尔投影中,手性中心显示为两条垂直线的交点。水平线代表平面外的键点,垂直线代表平面后方的键点。
It is very important to keep in mind that the lines in Fisher projection are not just bonds, they represent the bonds with specific spatial arrangements and stereochemistry.
重要的是要记住,费舍尔投影中的线不仅仅是键,它们代表具有特定空间排列和立体化学的键。
Assigning an R/S Configuration in a Fisher projection
在 Fisher 投影中分配 R/S 配置
Taking the following compound as an example:
以下面的化合物为例:
Assign group priority as we usually do.
像我们通常做的那样分配组优先级。
If the lowest priority group (#4 group) is on a vertical bond, determine the priority decrease direction from #1→#2→#3 as usual to get the configuration; clockwise is R and counterclockwise is S.
如果最低优先级组(#4组)在垂直键上,则照常确定优先级下降方向#1→#2→#3来获取配置;顺时针为R,逆时针为S。
So, the example here is an R-isomer, and the complete name of the compound is (R)-2-chlorobutane.
因此,这里的例子是R-异构体,该化合物的完整名称是(R)-2-氯丁烷。
If the lowest priority group is on a horizontal bond (as is the case in the following structure), determine the priority decrease direction as in step 2, then reverse the answer to the opposite way to get the final configuration.
如果最低优先级组处于水平键上(如下结构中的情况),则按步骤 2 确定优先级降低方向,然后将答案反转到相反的方式以获得最终配置。
So, the example here is a S-isomer, and the complete name of the compound is (S)-2-chlorobutane.
因此,这里的例子是S-异构体,该化合物的完整名称是(S)-2-氯丁烷。
Exercises 5.6 练习5.6
Explain that why in step 3 of the above procedure, the answer should be reversed to get the final (actual) configuration?
解释一下为什么在上述过程的步骤 3 中,应该颠倒答案以获得最终(实际)配置?
Answers to Chapter 5 Practice Questions第 5 章练习题答案
Exercises 5.7: Indicate the configuration of the following structures.
练习5.7:指出下列结构的配置。
Properties of a Fisher projection:
Fisher 投影的属性:
1. One switch (interchange) of two groups in a Fisher projection inverts the configuration, and two switches bring the original isomer back.
1.费舍尔投影中两组的一个开关(互换)使构型反转,两个开关使原来的异构体恢复。
For the above structures:
对于上述结构:
one switch of A leads to B, and A and B are enantiomers.
A的一个开关导致B,并且A和B是对映体。one switch of B leads to C, and B and C are enantiomers.
B的一个开关导致C,并且B和C是对映体。two switches of C leads to A, and A and C are identical.
C的两个开关通向A,A和C是相同的。
2. Rotate the Fisher projection 180º to get the same structure, with the configuration retained.
2. 将 Fisher 投影旋转 180° 以获得相同的结构,并保留配置。
A 180º rotation of A leads to B, and A and B are identical.
A旋转180°得到B,A和B相等。
3. Rotate the Fisher projection 90º to get the configuration inverted.
3. 将 Fisher 投影旋转 90° 以反转配置。
90º rotation of A leads to B, and A and B are enantiomers.
A旋转90°得到B,A和B是对映体。
Do NOT rotate the Fisher projection 90º, unless you have to. Keep in mind that the configuration gets inverted by a 90º rotation.
除非必要,否则请勿将 Fisher 投影旋转 90°。请记住,旋转 90° 后配置会发生反转。
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