(1S,1'R)-1,8-diethyl-1-(1',2'-diacetyloxy)ethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole | 241803-49-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (1S,1'R)-1,8-diethyl-1-(1',2'-diacetyloxy)ethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole
• 英文别名: [(2R)-2-acetyloxy-2-[(1S)-1,8-diethyl-4,9-dihydro-3H-pyrano[3,4-b]indol-1-yl]ethyl] acetate
• CAS: 241803-49-6
• 化学式: C₂₁H₂₇NO₅
• 分子量: 373.449
• InChiKey: OTTAOIVQWWGFAP-WIYYLYMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  77.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,1'R)-1,8-diethyl-1-(1',2'-diacetyloxy)ethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole 在 吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 9-borabicyclo[3.3.1]nonane dimer 、 三氟化硼乙醚 、 sodium hydride 、 magnesium bromide ethyl etherate 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 异丙醚 为溶剂， 生成 (1R)-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-1-ethanol
  参考文献：
  名称：

  The Formal Synthesis of Chiral Etodolac Using Chiral 1,2-Di(alkylcarbonyl)oxypentan-3-one as Chiral Building Block

  摘要：

  A stereoselective synthesis of (+)- and (-)-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-1-ethanols (31) and (32), the key intermediates for chiral etodolac was executed in seven steps starting from the asymmetric cyclization of (2R)-1,2-di(acetyloxypentan)-3-one (5) or (2R)-1,2-di(propionyloxypentan)-3-one (6) and 7-ethyltryptophol (7). Some unexpected transformations are also described.

  DOI：

  10.3987/com-98-8456
• 作为产物：
  描述：

  (4R)-1-(2,2-dimethyl)-(1,3)dioxolan-4-ylpropan-1-ol 在 吡啶 、 草酰氯 、 三氟化硼乙醚 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 76.33h， 生成 (1S,1'R)-1,8-diethyl-1-(1',2'-diacetyloxy)ethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole
  参考文献：
  名称：

  The Formal Synthesis of Chiral Etodolac Using Chiral 1,2-Di(alkylcarbonyl)oxypentan-3-one as Chiral Building Block

  摘要：

  A stereoselective synthesis of (+)- and (-)-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-1-ethanols (31) and (32), the key intermediates for chiral etodolac was executed in seven steps starting from the asymmetric cyclization of (2R)-1,2-di(acetyloxypentan)-3-one (5) or (2R)-1,2-di(propionyloxypentan)-3-one (6) and 7-ethyltryptophol (7). Some unexpected transformations are also described.

  DOI：

  10.3987/com-98-8456

文献信息

• The Formal Synthesis of Chiral Etodolac Using Chiral 1,2-Di(alkylcarbonyl)oxypentan-3-one as Chiral Building Block
  作者：Shan-Yen Chou、Chin-Lu Tseng、Shyh-Fong Chen

  DOI：10.3987/com-98-8456

  日期：——

  A stereoselective synthesis of (+)- and (-)-(1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-1-ethanols (31) and (32), the key intermediates for chiral etodolac was executed in seven steps starting from the asymmetric cyclization of (2R)-1,2-di(acetyloxypentan)-3-one (5) or (2R)-1,2-di(propionyloxypentan)-3-one (6) and 7-ethyltryptophol (7). Some unexpected transformations are also described.