(1R)-1-[(2R,3R)-3-methyloxiran-2-yl]pentan-1-ol | 4798-68-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R)-1-[(2R,3R)-3-methyloxiran-2-yl]pentan-1-ol
• CAS: 4798-68-9；84049-79-6；84049-80-9；142794-43-2；142794-44-3
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: SEHZTEMYUSPLDG-PRJMDXOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  10.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.76
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1R)-1-[(2R,3R)-3-methyloxiran-2-yl]pentan-1-ol 、 diethyl(phenylethynyl)aluminum 以20%的产率得到
  参考文献：
  名称：

  SUZUKI, TOSHIFUMI;SAIMOTO, HIROYUKI;TOMIOKA, HIROKI;OSHIMA, KOICHIRO;NOZA+, TETRAHEDRON LETT., 1982, 23, N 35, 3597-3600

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-1-((2R,3S)-3-Methyl-3-trimethylsilanyl-oxiranyl)-pentan-1-ol 在 cesium fluoride 作用下， 生成 (1R)-1-[(2R,3R)-3-methyloxiran-2-yl]pentan-1-ol
  参考文献：
  名称：

  The role of trimethylsilyl group in highly stereoselective eposidation of allylic alcohols

  摘要：

  DOI：

  10.1016/s0040-4039(00)87622-4

文献信息

• Stereo- and regioselectivity in iodo diol formation from acyclic allylic alcohols
  作者：A. Richard Chamberlin、Robert L. Mulholland

  DOI：10.1016/0040-4020(84)80012-5

  日期：1984.1

  with a variety of acyclic allylic alcohols was investigated. Both aqueous iodine and acetylhypoiodite convert certain alkenols into iodo diols and acetoxy iodo alcohols, respectively, with regio- and stereoselectivities as high as 99%. Protection of the alcohol group lowers the selectivity only slightly. Structural factors that control the regioselectivity ofiodohydrin formation in these substrates

  研究了亲电试剂与各种无环烯丙基醇的反应。碘水溶液和乙酰次碘水溶液都将某些烯醇分别转化为碘二醇和乙酰氧基碘醇，其区域和立体选择性高达99％。醇基的保护仅稍微降低了选择性。已经描述了控制这些底物中碘醇形成的区域选择性的结构因素。一些碘代二醇已被脱碘，说明了一个简单的两步程序即可将烯丙基醇转化为苏-1，3-二醇。
• Stereoselective reduction of α,β-epoxy ketones with sodium borohydride in the presence of calcium chloride or lanthanum chloride. A practical preparation of erythro-α,β-epoxy alcohols
  作者：Masahiko Taniguchi、Hideaki Fujii、Koichiro Oshima、Kiitiro Utimoto

  DOI：10.1016/0040-4020(94)00967-y

  日期：1995.1

  erythro-Epoxy alcohols were prepared with high stereoselectivity by NaBH4 reduction of the corresponding α,β-epoxy ketones in the presence of calcium chloride or lanthanum chloride regardless of the substituents on the epoxide ring.

  通过在氯化钙或氯化镧存在下，与环上的取代基无关的NaBH 4还原相应的α，β-环氧酮，可以高立体选择性制备赤-环氧醇。
• Stereoselective Reduction of α,β-Epoxy Ketones into erythro-α,β-Epoxy Alcohols with Sodium Borohydride in the Presence of Calcium Chloride
  作者：Hideaki Fujii、Koichiro Oshima、Kiitiro Utimoto

  DOI：10.1246/cl.1992.967

  日期：1992.6

  erythro-α,β-Epoxy alcohols were prepared with high stereoselectivity by sodium borohydride reduction of the corresponding α,β-epoxy ketones in the presence of calcium chloride or manganese(II) chloride regardless of the substituents on the epoxide ring.

  无论环氧化物环上的取代基如何，在氯化钙或氯化锰 (II) 存在下，通过硼氢化钠还原相应的 α,β-环氧酮，以高立体选择性制备赤型-α,β-环氧醇。
• Oxidation of allylic alcohols by dimethyldioxirane: Competition reaction between epoxidation and C-H insertion
  作者：Waldemar Adam、Frank Prechtl、Markus J. Richter、Alexander K. Smerz

  DOI：10.1016/s0040-4039(00)61350-3

  日期：1993.1

  Epoxidation of allylic alcohols with dimethyldioxirane is accompanied by oxidation of the hydroxy functionality; thus enone formation increases with decreasing substitution at the C-C double bond; nonetheless, selective epoxidation can be obtained by acylation of the alcohol functionality.