exo-10,10-diphenyl-10-methoxymethyl-7,7-dimethylbicyclo-[2.2.1]heptane-2-ol | 249739-60-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: exo-10,10-diphenyl-10-methoxymethyl-7,7-dimethylbicyclo-[2.2.1]heptane-2-ol
• 英文别名: (1S,2R,4R)-1-[methoxy(diphenyl)methyl]-7,7-dimethylbicyclo[2.2.1]heptan-2-ol
• CAS: 249739-60-4
• 化学式: C₂₃H₂₈O₂
• 分子量: 336.474
• InChiKey: XWQIEVRJOODPHZ-KCZVDYSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  exo-10,10-diphenyl-10-methoxymethyl-7,7-dimethylbicyclo-[2.2.1]heptane-2-ol 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 27.33h， 生成
  参考文献：
  名称：

  樟脑衍生助剂的合成及其在不对称 Darzens 反应中的应用

  摘要：

  通过一条高效、短的通用路线合成了一种现成的手性樟脑衍生助剂。在碱存在下，助剂与醛的 Darzens 反应得到几乎完全非对映控制和高产率的缩水甘油酯。

  DOI：

  10.3184/174751913x13737254410429
• 作为产物：
  描述：

  exo-10,10-diphenyl-10-hydroxymethyl-7,7-dimethylbicyclo[2.2.1]heptane-2-one 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 exo-10,10-diphenyl-10-methoxymethyl-7,7-dimethylbicyclo-[2.2.1]heptane-2-ol
  参考文献：
  名称：

  樟脑衍生助剂的合成及其在不对称 Darzens 反应中的应用

  摘要：

  通过一条高效、短的通用路线合成了一种现成的手性樟脑衍生助剂。在碱存在下，助剂与醛的 Darzens 反应得到几乎完全非对映控制和高产率的缩水甘油酯。

  DOI：

  10.3184/174751913x13737254410429

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。
• Novel Camphor-Derived Chiral Auxiliaries:  Significant Solvent and Additive Effects on Asymmetric Reduction of Chiral α-Keto Esters
  作者：Ying-Yuan Chu、Chia-Sheng Yu、Chiou-Juy Chen、Kung-Shuo Yang、Jung-Chaing Lain、Chun-Hui Lin、Kwunmin Chen

  DOI：10.1021/jo9902188

  日期：1999.9.1

  Stereoselective reduction of various alpha-keto esters 5a-d derived from exo-10,10-diphenyl-2,10-camphanediol 4a and exo-10,10-diphenyl-10-methoxy-2-camphanol 4b is described. High to excellent diastereomeric excess (99% de) with good chemical yields is obtained. The sense of stereoselectivity as a function of C10 modification is remarkable. Further, in the case of 5d, both diastereomers of a-hydroxyl esters can be obtained with excellent optical purity by the appropriate choice of reaction conditions. The influence of the solvents and additives on the reaction course has been investigated.
• On the scope of diastereoselective aziridination of various chiral auxiliaries derived N- and O-enones with N-aminophthalimide in the presence of lead tetraacetate
  作者：Pei-Wen Duan、Ching-Chen Chiu、Wei-Der Lee、Li Shiue Pan、Uppala Venkatesham、Zheng-Hao Tzeng、Kwunmin Chen

  DOI：10.1016/j.tetasy.2008.02.028

  日期：2008.4

  The treatment of a range of N- and O-enones derived from various camphor-based chiral auxiliaries A-D with N-aminoplithalimide in the presence of lead tetraacetate is described. In general, N-phtbalimidoaziridines were obtained with high diastereo-selectivities (up to 98% de) and chemical yields (up to 95%) when 10,10-diphenyl-2,10-camphanediol A derived O-enones with a range of substituents were used under the same reaction conditions. Excellent stereoselectivity was obtained when the N-tosyl camphorpyrazolidinone E derived acrylate was used. The absolute configuration of the new stereogenic center(s) of the major diastereomer was established by X-ray crystallographic analysis. Chiral auxiliary cleavage was achieved under mild reaction conditions. A model to explain the stereochemical induction is also proposed. (c) 2008 Elsevier Ltd. All rights reserved.