(1S,9S,10R,14R)-4-methoxy-1,12,12-trimethyl-11,13-dioxa-8-azatetracyclo[7.6.0.02,7.010,14]pentadeca-2(7),3,5-trien-9-ol | 332913-33-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (1S,9S,10R,14R)-4-methoxy-1,12,12-trimethyl-11,13-dioxa-8-azatetracyclo[7.6.0.02,7.010,14]pentadeca-2(7),3,5-trien-9-ol
• CAS: 332913-33-4
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: YNFFTGUJXYMGAO-LUYZLQTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,9S,10R,14R)-4-methoxy-1,12,12-trimethyl-11,13-dioxa-8-azatetracyclo[7.6.0.02,7.010,14]pentadeca-2(7),3,5-trien-9-ol 在 盐酸 、 sodium periodate 、 lithium aluminium tetrahydride 、 三乙酰氧基硼氢化钠 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 5-methoxy-3a,8-dimethyl-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]indole
  参考文献：
  名称：

  7,7-Dimethyl-6,8-dioxabicyclo[3.3.0]oct-3-en-2-one as a synthetic equivalent of ketodicyclopentadiene: a new route to (−)-physostigmine, (−)-physovenine, and (−)-aphanorphine

  摘要：

  A new diastercocontrolled route to three alkaloids having a quaternary benzylic stereogenic center, (-)-physostigmine, (-)-physovenine, and (-)-aphanorphine, has been developed using enantiopure 7,7-dimethyl-6,8-dioxabicyclo[3.3.0]oct-3-en-2-one as a synthetic equivalent of chiral cyclopentadienone. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02171-7
• 作为产物：
  描述：

  (3aR,6aR)-2,2,5-trimethyl-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one 在 palladium on activated charcoal 氢气 作用下， 以 吡啶 、 甲醇 、 水 为溶剂， 生成 (1S,9S,10R,14R)-4-methoxy-1,12,12-trimethyl-11,13-dioxa-8-azatetracyclo[7.6.0.02,7.010,14]pentadeca-2(7),3,5-trien-9-ol
  参考文献：
  名称：

  7,7-Dimethyl-6,8-dioxabicyclo[3.3.0]oct-3-en-2-one as a synthetic equivalent of ketodicyclopentadiene: a new route to (−)-physostigmine, (−)-physovenine, and (−)-aphanorphine

  摘要：

  A new diastercocontrolled route to three alkaloids having a quaternary benzylic stereogenic center, (-)-physostigmine, (-)-physovenine, and (-)-aphanorphine, has been developed using enantiopure 7,7-dimethyl-6,8-dioxabicyclo[3.3.0]oct-3-en-2-one as a synthetic equivalent of chiral cyclopentadienone. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02171-7