(1R,2R,3S,5R)-3-O-benzylpinanediol propionate | 318993-95-2

• 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: (1R,2R,3S,5R)-3-O-benzylpinanediol propionate
• 英文别名: [(1R,2R,3S,5R)-2,6,6-trimethyl-3-phenylmethoxy-2-bicyclo[3.1.1]heptanyl] propanoate
• CAS: 318993-95-2
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: UBLSXXQFGMXXJB-PDOICOKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-溴丙烯 、 (1R,2R,3S,5R)-3-O-benzylpinanediol propionate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 6.75h， 生成 (R)-2-Methyl-pent-4-enoic acid (1R,2R,3S,5R)-3-benzyloxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl ester 、 (S)-2-Methyl-pent-4-enoic acid (1R,2R,3S,5R)-3-benzyloxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl ester
  参考文献：
  名称：

  A pinene-based chiral auxiliary for α-alkylation and aldol reactions: an unexpected effect of the base on the stereoselectivity

  摘要：

  While the use of LDA as the base in the kinetic deprotonation step of the pinene-based ester 3 led to moderate diastereoselectivities in alpha -alkylation and aldol reactions, the use of LICA and LTMP resulted in a reduction in the anti/syn ratios and pi -facial selectivities. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00301-3
• 作为产物：
  描述：

  (1R,2R,3S,5R)-(-)-2,3-蒎烷二醇 在 silver cyanide 、 sodium hydride 作用下， 以 二甲基亚砜 、 苯 为溶剂， 反应 12.5h， 生成 (1R,2R,3S,5R)-3-O-benzylpinanediol propionate
  参考文献：
  名称：

  A pinene-based chiral auxiliary for α-alkylation and aldol reactions: an unexpected effect of the base on the stereoselectivity

  摘要：

  While the use of LDA as the base in the kinetic deprotonation step of the pinene-based ester 3 led to moderate diastereoselectivities in alpha -alkylation and aldol reactions, the use of LICA and LTMP resulted in a reduction in the anti/syn ratios and pi -facial selectivities. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00301-3

文献信息

• A pinene-based chiral auxiliary for α-alkylation and aldol reactions: an unexpected effect of the base on the stereoselectivity
  作者：Sergio Pinheiro、Clara B.S.S. Gonçalves、Marcelo B. de Lima、Florence M.C. de Farias

  DOI：10.1016/s0957-4166(00)00301-3

  日期：2000.9

  While the use of LDA as the base in the kinetic deprotonation step of the pinene-based ester 3 led to moderate diastereoselectivities in alpha -alkylation and aldol reactions, the use of LICA and LTMP resulted in a reduction in the anti/syn ratios and pi -facial selectivities. (C) 2000 Elsevier Science Ltd. All rights reserved.