(2R,10S)-1,2-Dihydroxy-8-methyl-10-(tetrahydro-pyran-2-yloxy)-undecan-6-one | 1026638-19-6

• 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: (2R,10S)-1,2-Dihydroxy-8-methyl-10-(tetrahydro-pyran-2-yloxy)-undecan-6-one
• 英文别名: (2R,10S)-1,2-dihydroxy-8-methyl-10-(oxan-2-yloxy)undecan-6-one
• CAS: 1026638-19-6
• 化学式: C₁₇H₃₂O₅
• 分子量: 316.438
• InChiKey: MJVPKCAGXHRUAV-OBKBAYEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,10S)-1,2-Dihydroxy-8-methyl-10-(tetrahydro-pyran-2-yloxy)-undecan-6-one 在 咪唑 、 盐酸 、 碘 、 三苯基膦 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 6.0h， 生成 8-Iodomethyl-2,4-dimethyl-1,7-dioxa-spiro[5.5]undecane
  参考文献：
  名称：

  A New Spiroketal Type from the Insect Kingdom

  摘要：

  The major component of the male or female dorsal abdominal gland secretion of the aposematic shield bug, Cantao parentum (White) (Hemiptera: Scutelleridae), is (2S,4R,6R,8S)-2,4,8-trimethyl-1,7-dioxaspiro-[5.5]undecane (23), the first example from the insect kingdom of a branched carbon chain spiroketal and the first spiroketal of any type from Hemiptera or lower insect orders.

  DOI：

  10.1021/jo00100a004
• 作为产物：
  描述：

  magnesium,pent-1-ene,bromide 在 重铬酸吡啶 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (2R,10S)-1,2-Dihydroxy-8-methyl-10-(tetrahydro-pyran-2-yloxy)-undecan-6-one
  参考文献：
  名称：

  A New Spiroketal Type from the Insect Kingdom

  摘要：

  The major component of the male or female dorsal abdominal gland secretion of the aposematic shield bug, Cantao parentum (White) (Hemiptera: Scutelleridae), is (2S,4R,6R,8S)-2,4,8-trimethyl-1,7-dioxaspiro-[5.5]undecane (23), the first example from the insect kingdom of a branched carbon chain spiroketal and the first spiroketal of any type from Hemiptera or lower insect orders.

  DOI：

  10.1021/jo00100a004

文献信息

• Synthesis and Stereochemistry of Insect Derived Spiroacetals with Branched Carbon Skeletons
  作者：Yong Q. Tu、Achim Hübener、Hesheng Zhang、Christopher J. Moore、Mary T. Fletcher、Patricia Hayes、Konrad Dettner、Wittko Francke、Christopher S. P. McErlean、William Kitching

  DOI：10.1055/s-2000-8232

  日期：——

  7-dioxoaspiro[5.5]undecane system and are certain stereoisomers of the 2,4,8-trimethyl derivative, from the aposematic shield bug, Cantao parentum (White), and a 2,2,8-trimethyl derivative from the rove beetle, Ontholestes murinus (L.). The 1,6-dioxaspiro[4.5]decane system is represented by a stereoisomer of the 2,3,7-trimethyl derivative in the Cantao species. The elucidation of their structures and stereochemistry

  大约三十种结构不同的螺缩醛已从昆虫中表征，但只有三种具有分支的碳骨架。两种基于 1,7-二氧杂螺[5.5]十一烷系统，是 2,4,8-三甲基衍生物的某些立体异构体，来自 aposematic shield bug, Cantao parentum (White)，以及 2,2,8-来自流浪甲虫 Ontholestes murinus (L.) 的三甲基衍生物。1,6-二氧杂螺[4.5]癸烷系统由Cantao物种中的2,3,7-三甲基衍生物的立体异构体表示。描述了通过光谱、合成和对映选择性气相色谱对它们的结构和立体化学的阐明。
• A New Spiroketal Type from the Insect Kingdom
  作者：Christopher J. Moore、Achim Huebener、Yong Q. Tu、William Kitching、Jeffrey R. Aldrich、Geoffrey K. Waite、Stefan Schulz、Wittko Francke

  DOI：10.1021/jo00100a004

  日期：1994.10

  The major component of the male or female dorsal abdominal gland secretion of the aposematic shield bug, Cantao parentum (White) (Hemiptera: Scutelleridae), is (2S,4R,6R,8S)-2,4,8-trimethyl-1,7-dioxaspiro-[5.5]undecane (23), the first example from the insect kingdom of a branched carbon chain spiroketal and the first spiroketal of any type from Hemiptera or lower insect orders.