(R)-(R)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-octan-1-ol | 208658-56-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-(R)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-octan-1-ol
• 英文别名: (1R)-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]octan-1-ol
• CAS: 208658-56-4
• 化学式: C₁₆H₃₀O₃
• 分子量: 270.412
• InChiKey: OVWLMSYLZNOSSU-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (R)-(R)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-octan-1-ol 在 sodium periodate 、 正丁基锂 、 sodium hydride 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 109.5h， 生成 (8R)-(6Z)-8-benzyloxypentadec-6-enoic acid
  参考文献：
  名称：

  Asymmetric synthesis of a cytotoxic amide of Telesto riisei

  摘要：

  An efficient synthesis of both the enantiomers of N-(2-phenylethyl)-8-hydroxypentadecacarboxamide using the cytotoxic principles of Telesto riisei has been formulated using cyclohexylideneglyceraldehyde 1 as the chiral template. A non-stereoselective Grignard addition to the aldehyde 1 gave the C-3 epimers of the required chiron, 3-alkylglycerol which were converted to the title compound via a standard sequence of reactions. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00091-3
• 作为产物：
  描述：

  HEPTYLMAGNESIUM BROMIDE 、 (R)-1,4-二氧杂螺[4,5]癸烷-2-甲醛 以 四氢呋喃 为溶剂， 反应 3.0h， 以50.6%的产率得到(S)-(R)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-octan-1-ol
  参考文献：
  名称：

  Asymmetric synthesis of a cytotoxic amide of Telesto riisei

  摘要：

  An efficient synthesis of both the enantiomers of N-(2-phenylethyl)-8-hydroxypentadecacarboxamide using the cytotoxic principles of Telesto riisei has been formulated using cyclohexylideneglyceraldehyde 1 as the chiral template. A non-stereoselective Grignard addition to the aldehyde 1 gave the C-3 epimers of the required chiron, 3-alkylglycerol which were converted to the title compound via a standard sequence of reactions. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00091-3

文献信息

• Asymmetric synthesis of a cytotoxic amide of Telesto riisei
  作者：Sivaraman Sankaranarayanan、Subrata Chattopadhyay

  DOI：10.1016/s0957-4166(98)00091-3

  日期：1998.4

  An efficient synthesis of both the enantiomers of N-(2-phenylethyl)-8-hydroxypentadecacarboxamide using the cytotoxic principles of Telesto riisei has been formulated using cyclohexylideneglyceraldehyde 1 as the chiral template. A non-stereoselective Grignard addition to the aldehyde 1 gave the C-3 epimers of the required chiron, 3-alkylglycerol which were converted to the title compound via a standard sequence of reactions. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.