cis-2-(4-methoxyphenyl)-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione | 151710-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: cis-2-(4-methoxyphenyl)-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione
• 英文别名: N-(4-methoxyphenyl)-cis-cyclohexane-1,2-dicarboximide；N-(4-methoxyphenyl)-cis-1,2-cyclohexanedicarboximide；cis-2-(p-methoxyphenyl)hexahydroisoindole-1,3-dione；2-(4-Methoxyphenyl)-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione；(3aS,7aR)-2-(4-methoxyphenyl)-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione
• CAS: 151710-38-2
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: WMTLJFNFFNSODY-BETUJISGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-2-(4-methoxyphenyl)-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione 在 甲醇 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 硫酸 、 S-1,1'-联-2-萘酚 作用下， 以 四氢呋喃 为溶剂， 反应 27.0h， 生成 (1S,6R)-8-oxabicyclo[4.3.0]nonan-7-one
  参考文献：
  名称：

  Enantioselective Reduction of meso-Cyclic-1,2-dicarboxylic Anhydrides and 1,2-Dicarboximides: Asymmetric Synthesis of Bicyclic Lactones and Hydroxylactams.

  摘要：

  手性双环内酯（3、8、9）和双环羟基内酰胺（10-13）是通过对meso-环状-1,2-二羧酸酐（1、4）和meso-环状-1,2-二羧酰胺（2）进行具有高对映选择性的还原反应，使用锂铝氢化物（LiAlH4）-醇（ROH）-（R）或（S）-1,1'-双-2-萘醇复合物[(R)或(S)-BINAL-H(ROH)]合成的。对羟基内酰胺（10-13）进行三乙基硅烷（Et3SiH）和三氟乙酸（CF3CO2H）的处理，得到了手性双环内酰胺（14、15），产率为定量。在高光学纯度下，用铈(IV)铵硝酸盐（CAN）顺利去除内酰胺（14、15）中的N-4-甲氧基苯基基团，得到相应的N-不取代内酰胺（16、17）。

  DOI：

  10.1248/cpb.42.9
• 作为产物：
  描述：

  1,2-cis-cyclohexanedicarboxylic anhydride 在 六甲基二硅氮烷 、 zinc(II) chloride 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 cis-2-(4-methoxyphenyl)-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione
  参考文献：
  名称：

  The crucial role of the nitrogen substituent in the desymmetrisation of cyclic meso-imides using B-Me and B-OMe oxazaborolidine catalysts

  摘要：

  Various cyclic meso-imides have been desymmetrised via enantioselective reduction using two chiral oxazaborolidine catalysts derived from (1R,2S)-cis-1-amino-indan-2-ol followed by the reduction of the hydroxylactarn product to give the gamma-lactam. The enantiomeric excesses were shown to be 27-99% by chiral HPLC and chiral GC of the gamma-lactam products with the nitrogen substituent playing a pivotal role in determining yield and selectivity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.051

文献信息

• Hydrogen bonding in cyclic imides and amide carboxylic acid derivatives from the facile reaction of<i>cis</i>-cyclohexane-1,2-carboxylic anhydride with<i>o</i>- and<i>p</i>-anisidine and<i>m</i>- and<i>p</i>-aminobenzoic acids
  作者：Graham Smith、Urs D. Wermuth

  DOI：10.1107/s0108270112030168

  日期：2012.9.15

  N—Car bond [dihedral angles between the benzene and isoindole rings = 51.55 (7)° in (II), 59.22 (12)° in (III) and 51.99 (14)° in (IV)]. Unlike (II), in which only weak intermolecular C—H...Oimide hydrogen bonding is present, the crystal packing of imides (III) and (IV) shows strong intermolecular carboxylic acid O—H...O hydrogen‐bonding associations. With (III), these involve imide O‐atom acceptors,

  开链的酰胺羧酸的结构外消旋-顺式-2 - [（2-甲氧基苯基）氨基甲酰基]环己烷-1-羧酸，C 15 ħ 19 NO 4，（I），和环状酰亚胺外消旋-顺式- 2-（4-甲氧基苯基）-3a，4,5,6,7,7a-六氢异吲哚-1,3-二酮，C 15 H 17 NO 3，（II），手性顺式-3-（1,3-二氧杂） -3a，4,5,6,7，hexahydroisoindol -2-基）苯甲酸，C 15 ħ 15 NO 4，（III），和外消旋-顺式-4-（1,3-二氧代3A，4,5-hexahydroisoindol -2-基）苯甲酸一水合物，C 15 ħ 15 NO 4 ·H 2 O，（IV）中，报告。在酰胺酸（I）中，苯基氨基甲酰基基团基本上是平面的[与最小二乘法平面的最大偏差= 0.060（1）Å对于酰胺O原子]，并且分子通过分子间环状羧基-羧基O-形成离散的中心对称二聚体H ... O氢键相互作用[图形符号R
• Highly Enantioselective Reduction of meso-Cyclic-1,2-dicarboximides. Asymmetric Synthesis of Bicyclic 2-Pyrrolidinone and Its 5-Hydroxy Congener
  作者：Kenji Matsuki、Hirozumi Inoue、Akihiko Ishida、Mikio Takeda、Masako Nakagawa、Tohru Hino

  DOI：10.3987/com-92-6307

  日期：——

  Bicyclic 5-hydroxy-2-pyrrolidinones (2a - f) were synthesized with high enantioselectivity by the reduction of meso underbar-cyclic- 1,2-dicarboximides (1a - f) with lithium aluminum hydride (LiAlH4)- methanol (MeOH)- 1,1'-bi-2-naphthol complex (BINAL-H). Treatment of 2a - f with triethylsilane (Et3SiH) and trifluoroacetic acid(CF3CO2H) gave optically active 2-pyrrolidinones (3a - f) in quantitative yields. For the absolute configuration correlation, 2a - d were converted into known lactones (4a - d).
• Enantioselective Reduction of meso-Cyclic-1,2-dicarboxylic Anhydrides and 1,2-Dicarboximides: Asymmetric Synthesis of Bicyclic Lactones and Hydroxylactams.
  作者：Kenji MATSUKI、Hirozumi INOUE、Akihiko ISHIDA、Mikio TAKEDA、Masako NAKAGAWA、Tohru HINO

  DOI：10.1248/cpb.42.9

  日期：——

  Chiral bicyclic lactones (3, 8, 9) and bicyclic hydroxylactams (10-13) were synthesized by highly enantioselective reduction of meso-cyclic-1, 2-dicarboxylic anhydrides (1, 4) and meso-cyclic-1, 2-dicarboximides (2) with lithium aluminum hydride (LiAlH4)-alcohol(ROH)-(R)- or (S)-1, 1'-bi-2-naphthol complex [(R)- or (S)-BINAL-H(ROH)]. Treatment of the hydroxylactams (10-13) with triethylsilane (Et3SiH) and trifluoroacetic acid (CF3CO2H) gave chiral bicyclic lactams (14, 15) in quantitative yields. Removal of the N-4-methoxyphenyl group of the lactams (14, 15) with cerium(IV) ammonium nitrate (CAN) proceeded smoothly to give the corresponding N-unsubstituted lactams (16, 17) in high optical purity.

  手性双环内酯（3、8、9）和双环羟基内酰胺（10-13）是通过对meso-环状-1,2-二羧酸酐（1、4）和meso-环状-1,2-二羧酰胺（2）进行具有高对映选择性的还原反应，使用锂铝氢化物（LiAlH4）-醇（ROH）-（R）或（S）-1,1'-双-2-萘醇复合物[(R)或(S)-BINAL-H(ROH)]合成的。对羟基内酰胺（10-13）进行三乙基硅烷（Et3SiH）和三氟乙酸（CF3CO2H）的处理，得到了手性双环内酰胺（14、15），产率为定量。在高光学纯度下，用铈(IV)铵硝酸盐（CAN）顺利去除内酰胺（14、15）中的N-4-甲氧基苯基基团，得到相应的N-不取代内酰胺（16、17）。
• The crucial role of the nitrogen substituent in the desymmetrisation of cyclic meso-imides using B-Me and B-OMe oxazaborolidine catalysts
  作者：Mike D. Barker、Rachel A. Dixon、Simon Jones、Barrie J. Marsh

  DOI：10.1016/j.tet.2006.09.051

  日期：2006.12

  Various cyclic meso-imides have been desymmetrised via enantioselective reduction using two chiral oxazaborolidine catalysts derived from (1R,2S)-cis-1-amino-indan-2-ol followed by the reduction of the hydroxylactarn product to give the gamma-lactam. The enantiomeric excesses were shown to be 27-99% by chiral HPLC and chiral GC of the gamma-lactam products with the nitrogen substituent playing a pivotal role in determining yield and selectivity. (c) 2006 Elsevier Ltd. All rights reserved.