(1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]heptane-1-carboxylic acid diisopropylamide | 122934-47-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]heptane-1-carboxylic acid diisopropylamide
• 英文别名: (1S,2R,4R)-2-hydroxy-7,7-dimethyl-N,N-di(propan-2-yl)bicyclo[2.2.1]heptane-1-carboxamide
• CAS: 122934-47-8
• 化学式: C₁₆H₂₉NO₂
• 分子量: 267.412
• InChiKey: BQGAGAOLRQQPQX-IOASZLSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]heptane-1-carboxylic acid diisopropylamide 在 lithium aluminium tetrahydride 作用下， 以84%的产率得到(1R,2R)-10-(diisopropylamino)isoborneol
  参考文献：
  名称：

  通过将二乙烯基锌催化不对称加成到醛中来对仲烯丙醇进行对映选择性合成。

  摘要：

  容易获得的手性三齿配体催化高度的Si二乙基- ，二-的-面选择性添加Ñ -propylzinc和，divinylzinc的更显著，以芳族和脂族醛，而二齿配体和施加逆转拓扑催化偏压。

  DOI：

  10.1016/s0040-4039(00)80834-5
• 作为产物：
  描述：

  (1S)-diisopropylketopinamide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以90%的产率得到(1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]heptane-1-carboxylic acid diisopropylamide
  参考文献：
  名称：

  通过将二乙烯基锌催化不对称加成到醛中来对仲烯丙醇进行对映选择性合成。

  摘要：

  容易获得的手性三齿配体催化高度的Si二乙基- ，二-的-面选择性添加Ñ -propylzinc和，divinylzinc的更显著，以芳族和脂族醛，而二齿配体和施加逆转拓扑催化偏压。

  DOI：

  10.1016/s0040-4039(00)80834-5

文献信息

• anti-Aldol reactions of chiral alcohol-substituted vinylogous urethanes and the synthesis of (−)-prelactone B
  作者：Yu-Jang Li、Hsiu-Yin Hung、Yu-Wei Liu、Pei-Jhen Lin、Hung-Jyun Huang

  DOI：10.1016/j.tet.2010.12.009

  日期：2011.2

  alcohol-substituted vinylogous urethanes, in which the double bond has E configuration was determined by single crystal X-ray analysis. In addition, we investigated the anti-aldol reactions of these chiral vinylogous urethane anions. The use of (1S,2R,4R)-1-(hydroxydiphenylmethyl)-7,7-dimethylbicyclo[2,2,1]-heptan-2-ol as a chiral auxiliary, provided the best enantioselectivities, and the resulting vinylogous urethane

  本文描述了一种方便有效的合成手性醇取代的乙烯基氨基甲酸酯的方法，其中通过单晶X射线分析确定了具有E构型的双键。另外，我们研究了这些手性乙烯基类氨基甲酸酯阴离子的抗醛醇缩合反应。使用（1 S，2 R，4 R）-1-（羟基二苯甲基）-7,7-二甲基双环[2,2,1]-庚-2-醇作为手性助剂，可提供最佳对映选择性，并且所得的乙烯基类氨基甲酸酯内酯可用于合成（-）-内酯B。讨论了主要对映异构体生成的合理机理。
• anti-Selective aldol reactions of chiral alcohol substituted γ-benzyloxyl vinylogous urethanes and the synthesis of 3-benzyloxyl-4-hydroxylalkan-2-ones
  作者：Yu-Jang Li、Chuan-Chung Chung、Pin-Zu Chen

  DOI：10.1016/j.tetasy.2017.10.003

  日期：2017.11

  The anti-selective aldol reaction of chiral alcohol-substituted gamma-benzyloxy vinylogous urethanes is described. The use of (1S,2R,4R)-1-(hydroxydiphenylmethyl)-7,7-dimethylbicyclo[2,2,1]-heptan-2-ol as a chiral auxiliary in the aldol reaction of a vinylogous urethane enolate was found to provide anti-products in good yields with moderate to excellent enantioselectivities. The major anti-vinylogous urethane lactones were transformed into 3-benzyloxyl-4-hydroxylalkan-2-ones in good yields. (C) 2017 Elsevier Ltd. All rights reserved.
• Asymmetric [2,3]-Wittig rearrangement of the dienolates of chiral secondary alcohol-substituted β-pyrrolidinyl-γ-allyloxyl-α,β-unsaturated esters: total synthesis of (+)-eldanolide
  作者：Yu-Jang Li、Guo-Ming Ho、Pin-Zu Chen

  DOI：10.1016/j.tetasy.2009.07.028

  日期：2009.8

  The asymmetric [2,3]-Wittig rearrangement of the dienolates of various chiral beta-pyrrolidinyl-gamma-allyloxyl-alpha,beta-unsaturated esters was investigated using different chiral secondary alcohol Substitutions. When (1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2,2,1]heptane-1-carboxylic acid diisopropylamide was used as chiral auxiliary, it provided the best enantioselectivity in the rearrangement. When various gamma-allyloxy substitutions underwent temperature and additive studies, 1,1-dimethylpropenoxy substitution was found to give the best enantioselectivity. The methodology was applied to the total synthesis of eldanolide. (C) 2009 Elsevier Ltd. All rights reserved.
• OPPOLZER, WOLFGANG;RADINOV, RUMEN N., TETRAHEDRON LETT., 29,(1988) N 44, C. 5645-5648
  作者：OPPOLZER, WOLFGANG、RADINOV, RUMEN N.

  DOI：——

  日期：——