(S)-2-[(S)-1-(methoxymethoxy)heptyl]oxirane | 850222-11-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (S)-2-[(S)-1-(methoxymethoxy)heptyl]oxirane
• 英文别名: 2-(1-methoxymethoxy)heptyl-oxirane；(2S)-2-[(1S)-1-(methoxymethoxy)heptyl]oxirane
• CAS: 850222-11-6
• 化学式: C₁₁H₂₂O₃
• 分子量: 202.294
• InChiKey: XHVIGKJCGQEEGT-QWRGUYRKSA-N

物化性质

• 沸点：
  257.1±15.0 °C(Predicted)
• 密度：
  0.971±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-[(S)-1-(methoxymethoxy)heptyl]oxirane 在 Pd-BaSO₄ 氢气 、 乙二胺 作用下， 以 喹啉 、 二甲基亚砜 、 苯 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 12.5h， 生成 (4S,5S)-5-(methoxymethyloxy)undec-1-en-4-ol
  参考文献：
  名称：

  Stereoselective synthesis of (−)-microcarpalide

  摘要：

  A highly convergent and efficient synthesis of (-)-microcarpalide, a 10-membered lactone displaying remarkable microfilament disrupting activity is described. Ring-closing metathesis and Sharpless asymmetric dihydroxylations are the key steps. Our strategy highlights the application of novel hydroxy lactone precursors for the stereoselective synthesis of (-)-microcarpalide. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.052
• 作为产物：
  描述：

  反-2-壬烯-1-醇 在 甲基磺酰胺 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 sodium hydroxide 、 N-氯代丁二酰亚胺 、 potassium dioxotetrahydroxoosmate(VI) 、 potassium carbonate 、 N,N-二异丙基乙胺 、 三苯基膦 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 18.0h， 生成 (S)-2-[(S)-1-(methoxymethoxy)heptyl]oxirane
  参考文献：
  名称：

  Total Synthesis of Microcarpalide

  摘要：

  An efficient, convergent approach for the total synthesis of microcarpalide (1) is described. The synthetic strategy features the Sharpless asymmetric dihydroxylation, regioselective epoxide opening with various nucleophiles such as a lithium acetylide and cuprates derived from the vinyl stannane and the vinyl iodide for the construction of a C7-C8 trans-double bond and Yamaguchi macrolactonization as the key steps.

  DOI：

  10.1021/jo050193e

文献信息

• Total synthesis of mycestericin A and its 14-epimer
  作者：Hiroyoshi Yamanaka、Kazuya Sato、Hideyuki Sato、Masatoshi Iida、Takeshi Oishi、Noritaka Chida

  DOI：10.1016/j.tet.2009.09.012

  日期：2009.11

  The total synthesis of mycestericin A (1) and its 14-epimer 34 is described herein. The Overman rearrangement of an allylic trichloroacetimidate derived from l-tartrate generated a tetra-substituted carbon with nitrogen and subsequent stereoselective transformations afforded the highly functionalized left-half segment, vinyl iodide. Cross-coupling of the vinyl iodide with a chiral organometallic species

  本文描述了mycestericin A（1）及其14-受体34的总合成。衍生自1-酒石酸酯的烯丙基三氯乙酰亚胺酸酯的超载重排产生了具有氮的四取代碳，随后的立体选择性转化提供了高度官能化的左半段碘乙烯。在Negishi或Suzuki-Miyaura偶联条件下，碘化乙烯与d-酒石酸合成的手性有机金属物质交叉偶联，然后脱保护，完成了1的总合成。还合成了Mycestericin A的14个表位，并比较了[α] D霉菌素A及其14-受体的过乙酰基γ-内酯衍生物的分子量值以及对1和34的降解研究充分证实了拟议的霉菌素A的绝对结构。
• Stereoselective synthesis of (−)-microcarpalide
  作者：Subhash P. Chavan、Cherukupally Praveen

  DOI：10.1016/j.tetlet.2005.01.052

  日期：2005.3

  A highly convergent and efficient synthesis of (-)-microcarpalide, a 10-membered lactone displaying remarkable microfilament disrupting activity is described. Ring-closing metathesis and Sharpless asymmetric dihydroxylations are the key steps. Our strategy highlights the application of novel hydroxy lactone precursors for the stereoselective synthesis of (-)-microcarpalide. (C) 2005 Elsevier Ltd. All rights reserved.
• Total Synthesis of Microcarpalide
  作者：Pradeep Kumar、S. Vasudeva Naidu

  DOI：10.1021/jo050193e

  日期：2005.5.1

  An efficient, convergent approach for the total synthesis of microcarpalide (1) is described. The synthetic strategy features the Sharpless asymmetric dihydroxylation, regioselective epoxide opening with various nucleophiles such as a lithium acetylide and cuprates derived from the vinyl stannane and the vinyl iodide for the construction of a C7-C8 trans-double bond and Yamaguchi macrolactonization as the key steps.