(1'S,2'S,3'S,6'R,7'R)-Spiro([1,3]dioxolane-2,10'-tricyclo[5.2.1.0^2,6]deca-4',8'-dien)-3'-ol | 62928-77-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1'S,2'S,3'S,6'R,7'R)-Spiro([1,3]dioxolane-2,10'-tricyclo[5.2.1.0^2,6]deca-4',8'-dien)-3'-ol
• 英文别名: (1'S,2'S,3'S,6'R,7'R)-spiro[1,3-dioxolane-2,10'-tricyclo[5.2.1.02,6]deca-4,8-diene]-3'-ol
• CAS: 62928-77-2
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: KJHBXDXFSPWVDP-SSRBZLIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1'S,2'S,3'S,6'R,7'R)-Spiro([1,3]dioxolane-2,10'-tricyclo[5.2.1.0^2,6]deca-4',8'-dien)-3'-ol 在 咪唑 、 sodium tetrahydroborate 、 sodium periodate 、 N-溴代丁二酰亚胺(NBS) 、 四氧化锇 、 Amberlyst 、 溶剂黄146 、 N-甲基吗啉氧化物 、 锌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Polycyclitols: Stereoselective synthesis of decalin and diquinane based polyols as potential glycomimics

  摘要：

  Stereoselective syntheses of novel, polyhydroxylated decalins and diquinanes (enantidpure) bearing ten and eight stereogenic centres, respectively, from readily available starting materials is reported. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01895-x
• 作为产物：
  描述：

  (1'S*,2'S*,3'S*,6'R*,7'R*)-Spiro([1,3]dioxolane-2,10'-tricyclo[5.2.1.0^2,6]deca-4',8'-diene)-3'-ol 以46%的产率得到(1'S,2'S,3'S,6'R,7'R)-Spiro([1,3]dioxolane-2,10'-tricyclo[5.2.1.0^2,6]deca-4',8'-dien)-3'-ol
  参考文献：
  名称：

  Enzymatic resolution of dioxygenated dicyclopentadienes: Enantiopure hydrindanes, hydroisoquinolones, diquinanes and application to a synthesis of (+)-coronafacic acid

  摘要：

  A 5, 10-dioxygenated-tricyclo[5.2.1.0(2,6)]decane derivative 6 has yielded to efficient enzymatic resolution to provide a range of chiral building blocks, whose absolute configuration has been determined through a total synthesis of naturally occuring (+)-coronafacic acid. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02465-4

文献信息

• A simple entry into enantiopure hydrindanes, hydroisoquinolones and diquinanes from 3,10-dioxygenated dicyclopentadienes: Application to the synthesis of (+)-coronafacic acid and a formal synthesis of (+)-coriolin
  作者：Goverdhan Mehta、D. Srinivasa Reddy

  DOI：10.1039/b009307f

  日期：——

  6]decane derivatives is reported. An efficient enzymatic kinetic resolution is employed through transesterification in the presence of lipase PS immobilized on Celite. Absolute configuration of the tricyclo[5.2.1.02,6]decan-10-one derivatives has been secured through correlation with (1R,2S)-1-aminoindan-2-ol. The promising utility of these enantiopure tricyclo[5.2.1.02,6]decane derivatives in synthesis

  据报道，现可得到对映体纯的3,10-双加氧的三环[5.2.1.0 2,6 ]癸烷衍生物。在固定在硅藻土上的脂肪酶PS存在下，通过酯交换反应可实现有效的酶动力学拆分。通过与（1 R，2 S）-1-氨基茚满-2-醇相关联，可以确保三环[5.2.1.0 2,6 ] decan-10-one衍生物的绝对构型。这些对映体纯的三环[5.2.1.0 2,6 ]癸烷衍生物在合成中的应用前景广阔，已通过制备几种光学纯的顺式-氢化茚15-18进行了证明，采用Haller-Bauer反应作为解开三降冰片烯的关键步骤。系统。这顺式-茚满（-）- 16已被进一步精制为天然产物（+）-可乐果酸（+）- 24。以有趣的顺序，分别通过衍生的恶唑烷29和32的光重排，将顺式-氢化丹酮（+）- 18转化为顺式-氢异喹诺酮（+）- 30和（+）- 33。氢异喹啉酮（+）- 30和（+）- 33可以用作合成复杂的吲哚生物碱的有用
• Polycyclitols: Stereoselective synthesis of enantiopure polyhydroxylated hydrindanes (annulated carbasugars)
  作者：Goverdhan Mehta、D.Srinivasa Reddy

  DOI：10.1016/s0040-4039(99)01894-8

  日期：1999.12

  Employing readily available 5,10-dioxygenated-tricyclo[5.2.1.0(2,6)] decane derivatives, synthesis of several polyhydroxylated hydrindanes, constituting a new family of annulated carbasugars has been accomplished in a stereoselective manner. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• Enzymatic resolution of dioxygenated dicyclopentadienes: Enantiopure hydrindanes, hydroisoquinolones, diquinanes and application to a synthesis of (+)-coronafacic acid
  作者：Goverdhan Mehta、D.Srinivasa Reddy

  DOI：10.1016/s0040-4039(98)02465-4

  日期：1999.1

  A 5, 10-dioxygenated-tricyclo[5.2.1.0(2,6)]decane derivative 6 has yielded to efficient enzymatic resolution to provide a range of chiral building blocks, whose absolute configuration has been determined through a total synthesis of naturally occuring (+)-coronafacic acid. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Polycyclitols: Stereoselective synthesis of decalin and diquinane based polyols as potential glycomimics
  作者：Goverdhan Mehta、D.Srinivasa Reddy、S.S. Ramesh、Utpal Tatu

  DOI：10.1016/s0040-4039(99)01895-x

  日期：1999.12

  Stereoselective syntheses of novel, polyhydroxylated decalins and diquinanes (enantidpure) bearing ten and eight stereogenic centres, respectively, from readily available starting materials is reported. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.