(R)-2-[4-(4-methoxybenzyloxy)butyl]oxirane | 1201898-67-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-[4-(4-methoxybenzyloxy)butyl]oxirane
• 英文别名: (2R)-2-[4-[(4-methoxyphenyl)methoxy]butyl]oxirane
• CAS: 1201898-67-0
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: CQTGLUJSHRRDIM-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  (R)-2-[4-(4-methoxybenzyloxy)butyl]oxirane 在 咪唑 、 lithium aluminium tetrahydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 (S)-5-((tert-butyldiphenylsilyl)oxy)hexan-1-ol
  参考文献：
  名称：

  Total synthesis of two γ-butyrolactone containing compounds (Z,11S)-3,4-trans-11-hydroxy-3-methyldodec-cis-6-en-4-olide and (Z)-3,4-trans-11-oxo-3-methyldodec-cis-6-en-4-olide

  摘要：

  The first total synthesis of (2,11S)-3,4-trans-11-hydroxy-3-methyldodec-cis-6-en-4-olide and (2)-3,4-trans-11-oxo-3-methyldodec-cis-6-en-4-olide was accomplished using Jacobsen hydrolytic kinetic resolution, Ohira-Bestmann reaction, regioselective allcyne addition to terminal carbon atom of epoxide, intramolecular TEMPO/BAIB mediated oxidative lactonization and partial hydrogenation as the key steps. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.021
• 作为产物：
  描述：

  4-甲氧基苄醇 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 32.0h， 生成 (R)-2-[4-(4-methoxybenzyloxy)butyl]oxirane
  参考文献：
  名称：

  Total synthesis of two γ-butyrolactone containing compounds (Z,11S)-3,4-trans-11-hydroxy-3-methyldodec-cis-6-en-4-olide and (Z)-3,4-trans-11-oxo-3-methyldodec-cis-6-en-4-olide

  摘要：

  The first total synthesis of (2,11S)-3,4-trans-11-hydroxy-3-methyldodec-cis-6-en-4-olide and (2)-3,4-trans-11-oxo-3-methyldodec-cis-6-en-4-olide was accomplished using Jacobsen hydrolytic kinetic resolution, Ohira-Bestmann reaction, regioselective allcyne addition to terminal carbon atom of epoxide, intramolecular TEMPO/BAIB mediated oxidative lactonization and partial hydrogenation as the key steps. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.021

文献信息

• First asymmetric total synthesis of aspinolide A
  作者：Partha Sarathi Chowdhury、Priti Gupta、Pradeep Kumar

  DOI：10.1016/j.tetlet.2009.09.151

  日期：2009.12

  The first total synthesis of aspinolide A has been achieved using ring-closing metathesis as a key step. The stereogenic centers were generated by means of hydrolytic kinetic resolution (HKR) of racemic epoxides.

  Aspinolide A的第一个全合成方法是使用闭环复分解作为关键步骤。立体异构中心是通过外消旋环氧化物的水解动力学拆分（HKR）生成的。
• Synthesis of (R)-Coniine and (S)-Coinicine via Organocatalytic α-Aminoxyl­ation of an Aldehyde
  作者：Pradeep Kumar、Nagendra Kondekar

  DOI：10.1055/s-0030-1257869

  日期：2010.9

  A short and efficient synthesis of the indolizidine alkaloid (S)-coinicine has been achieved using organocatalytic sequential α-aminoxylation and Horner-Wadsworth-Emmons olefination of an aldehyde catalyzed by l-proline. Similarly, a common organocatalytic α-aminoxylation route has been developed for the asymmetric synthesis of both (R)-coniine and (S)-coinicine. synthesis - organocatalysis - sequential

  的吲哚里生物碱的简短和有效的合成（小号）-coinicine已经使用有机催化顺序α-aminoxylation和由催化的醛的霍纳-沃兹沃思-埃蒙斯烯实现升-脯氨酸。类似地，已经开发了一种常见的有机催化α-氨基羟化途径，用于（R）-亚氨酸和（S）-椰氨酸的不对称合成。 合成-有机催化-顺序反应-脯氨酸-铁杉生物碱
• Total synthesis of two γ-butyrolactone containing compounds (Z,11S)-3,4-trans-11-hydroxy-3-methyldodec-cis-6-en-4-olide and (Z)-3,4-trans-11-oxo-3-methyldodec-cis-6-en-4-olide
  作者：Rajesh Nomula、Galla Raju、Palakodety Radha Krishna

  DOI：10.1016/j.tetlet.2014.09.021

  日期：2014.10

  The first total synthesis of (2,11S)-3,4-trans-11-hydroxy-3-methyldodec-cis-6-en-4-olide and (2)-3,4-trans-11-oxo-3-methyldodec-cis-6-en-4-olide was accomplished using Jacobsen hydrolytic kinetic resolution, Ohira-Bestmann reaction, regioselective allcyne addition to terminal carbon atom of epoxide, intramolecular TEMPO/BAIB mediated oxidative lactonization and partial hydrogenation as the key steps. (C) 2014 Elsevier Ltd. All rights reserved.