[2S-[2α,3α,4α,5α(3aS*,6R*,7aR*)]]-3,4-pyrrolidinecarboxylic acid, 2-phenyl-5-[(tetrahydro-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl)-carbonyl]-dimethyl ester, S,S-dioxide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [2S-[2α,3α,4α,5α(3aS*,6R*,7aR*)]]-3,4-pyrrolidinecarboxylic acid, 2-phenyl-5-[(tetrahydro-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl)-carbonyl]-dimethyl ester, S,S-dioxide
• 英文别名: dimethyl (2R,3S,4R,5S)-2-[(1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-5-phenylpyrrolidine-3,4-dicarboxylate；dimethyl (2R,3S,4R,5S)-2-[(1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-5-phenylpyrrolidine-3,4-dicarboxylate
• 化学式: C₂₅H₃₂N₂O₇S
• 分子量: 504.604
• InChiKey: BCUNXKPBFWDWHY-CSQXBBDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [2S-[2α,3α,4α,5α(3aS*,6R*,7aR*)]]-3,4-pyrrolidinecarboxylic acid, 2-phenyl-5-[(tetrahydro-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl)-carbonyl]-dimethyl ester, S,S-dioxide 在 lithium hydroxide 、 氯化亚砜 作用下， 以 甲醇 为溶剂， 生成 (2S,3S,4R,5S)-2,3,4-tri(carbomethoxy)-5-phenylpyrrolidine
  参考文献：
  名称：

  New Zinc(II)-Based Catalyst for Asymmetric Azomethine Ylide Cycloaddition Reactions

  摘要：

  A new chiral aziridino alcohol ligand for zinc(II)-catalyzed azomethine ylide cycloadditions is described. In the presence of this catalyst, N-arylidene glycine methyl esters react with a variety of dipolarophiles to give substituted pyrrolidines in very good to excellent chemical yields and up to 95% ee. The absolute sense of asymmetric induction appears to be dipolarophile-dependent.

  DOI：

  10.1021/ol061521f
• 作为产物：
  描述：

  苯甲醛 、 马来酸二甲酯 、 2-Amino-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-ethanone 在 4 A molecular sieve 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 [2S-[2α,3α,4α,5α(3aS*,6R*,7aR*)]]-3,4-pyrrolidinecarboxylic acid, 2-phenyl-5-[(tetrahydro-8,8-dimethyl-3H-3a,6-methano-2,1-benzisothiazol-1(4H)-yl)-carbonyl]-dimethyl ester, S,S-dioxide
  参考文献：
  名称：

  Auxiliary controlled 1,3-dipolar cycloadditions of chiral stabilized azomethine ylides

  摘要：

  DOI：

  10.1021/jo00080a002

文献信息

• Stereocontrolled 1,3-dipolar cycloadditions using Oppolzer's camphor sultam as the chiral auxiliary for carbonyl stabilized azomethine ylides
  作者：Philip Garner、Özdemir Dogan、Wiley J. Youngs、Vance O. Kennedy、John Protasiewicz、Rebecca Zaniewski

  DOI：10.1016/s0040-4020(00)00998-4

  日期：2001.1

  Two complementary approaches to substituted pyrrolidines via stereocontrolled 1,3-dipolar cycloaddition reactions of chiral azomethine ylides are described. In one approach, chiral azomethine ylides were generated by thermolysis of aziridine carboxylate sultams and trapped with a variety of dipolarophiles to give good yields of the corresponding cycloadducts. In the second approach, chiral azomethine

  描述了通过手性偶氮甲亚胺基团的立体控制的1，3-偶极环加成反应来取代吡咯烷的两种互补方法。在一种方法中，通过将氮丙啶羧酸酯的sultams热解产生手性的甲亚胺基团，并用多种偶极亲和剂捕获，以得到相应环加合物的良好收率。在第二种方法中，通过“亚胺互变异构化”从甘氨酰磺胺生成手性偶氮甲亚胺，并用双极性亲和剂捕获，得到相应环加合物的良好收率。
• Garner Philip, Dogan Ozdemir, J. Org. Chem, 59 (1994) N 1, S 4-6
  作者：Garner Philip, Dogan Ozdemir

  DOI：——

  日期：——
• New Zinc(II)-Based Catalyst for Asymmetric Azomethine Ylide Cycloaddition Reactions
  作者：Özdemir Dogan、Hasan Koyuncu、Philip Garner、Adnan Bulut、Wiley J. Youngs、Matthew Panzner

  DOI：10.1021/ol061521f

  日期：2006.10.1

  A new chiral aziridino alcohol ligand for zinc(II)-catalyzed azomethine ylide cycloadditions is described. In the presence of this catalyst, N-arylidene glycine methyl esters react with a variety of dipolarophiles to give substituted pyrrolidines in very good to excellent chemical yields and up to 95% ee. The absolute sense of asymmetric induction appears to be dipolarophile-dependent.
• Auxiliary controlled 1,3-dipolar cycloadditions of chiral stabilized azomethine ylides
  作者：Philip Garner、Ozdemir Dogan

  DOI：10.1021/jo00080a002

  日期：1994.1