(E)-2,3-epoxytetradecan-1-ol

• 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: (E)-2,3-epoxytetradecan-1-ol
• 英文别名: (2S-trans)-3-Undecyloxirane methanol；[(2S,3S)-3-undecyloxiran-2-yl]methanol
• 化学式: C₁₄H₂₈O₂
• 分子量: 228.375
• InChiKey: COPUKNMSKSHUJH-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2,3-epoxytetradecan-1-ol 在 吡啶 、 红铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 20.0h， 生成 (3S)-1,3-Bis<(S)-α-methoxy-α-(trifluoromethyl)phenylacetoxy>tetradecane
  参考文献：
  名称：

  Sugiyama, Shigeo; Honda, Masanori; Komori, Tetsuya, Liebigs Annalen der Chemie, 1990, # 11, p. 1069 - 1078

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-2-tetradecen-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二异丙酯 作用下， 生成 (E)-2,3-epoxytetradecan-1-ol
  参考文献：
  名称：

  Total synthesis of enantiomers of (3Z,6Z)-cis-9,10-epoxy 1,3,6-henicosatriene — the pheromonal component of Diacrisia obliqua

  摘要：

  Synthesis of enantiomers of (3Z,6Z)-cis-9,10-epoxy 1,3,6-henicosatriene, the pheromonal component of Diacrisia obliqua was achieved through alkylative epoxide rearrangement and stereoselective Wittig olefination reactions as the key steps. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00389-5

文献信息

• 2,3-epoxy derivatives as anti retrovital chemotherapeutic agents
  申请人：The United States of America as represented by the Secretary of the

  公开号：US05190969A1

  公开（公告）日：1993-03-02

  The present invention is related to compounds, compositions and methods of treating viral infections. Compounds of the present invention have the following general formula: ##STR1## wherein R is selected from --CH.sub.2 OH, --CO.sub.2 R.sup.2, --CONR.sup.3 R.sup.4, or COR.sup.5, wherein R.sup.2 is hydrogen or a lower alkyl group, R.sup.3 and R.sup.4 are each independently hydrogen or a lower alkyl group, R.sup.5 is an amino acid residue bound via a terminal nitrogen or peptide having at least two amino acid residues; and wherein R.sup.1 is C.sub.5 -C.sub.13 alkyl, aryl, aralkyl, aralkyl(lower alkyl) ether, or C.sub.5 -C.sub.13 alkyl (lower alkyl)ether.

  本发明涉及化合物、组合物和治疗病毒感染的方法。本发明的化合物具有以下通用式：##STR1## 其中R从--CH.sub.2 OH、--CO.sub.2 R.sup.2、--CONR.sup.3 R.sup.4或COR.sup.5中选择，其中R.sup.2是氢或低级烷基，R.sup.3和R.sup.4各自独立地是氢或低级烷基，R.sup.5是通过末端氮或至少具有两个氨基酸残基的肽结合的氨基酸残基；R.sup.1是C.sub.5-C.sub.13烷基、芳基、芳基烷基、芳基烷基（低级烷基）醚或C.sub.5-C.sub.13烷基（低级烷基）醚。
• 2,3-epoxy alcohols, acids and derivatives as anti retroviral
  申请人：The United States of America as represented by the Department of Health

  公开号：US06153589A1

  公开（公告）日：2000-11-28

  The present invention is related to compounds, compositions and methods of treating viral infections. Compounds of the present invention have the following general formula: ##STR1## wherein R is selected from --CH.sub.2 OH, --CO.sub.2 R.sup.2, --CONR.sup.3 R.sup.4, or COR.sup.5, wherein R.sup.2 is hydrogen or a lower alkyl group, R.sup.3 and R.sup.4 are each independently hydrogen or a lower alkyl group, R.sup.5 is an amino acid residue bound via a terminal nitrogen or peptide having at least two amino acid residues; and wherein R.sup.1 is C.sub.5 -C.sub.13 alkyl, aryl, aralkyl, aralkyl(lower alkyl)ether, or C.sub.5 -C.sub.13 alkyl(lower alkyl)ether.

  本发明涉及化合物、组合物和治疗病毒感染的方法。本发明的化合物具有以下一般式：##STR1## 其中，R从--CH.sub.2 OH、--CO.sub.2 R.sup.2、--CONR.sup.3 R.sup.4或COR.sup.5中选择，其中R.sup.2为氢或低碳基，R.sup.3和R.sup.4各自独立地为氢或低碳基，R.sup.5为通过末端氮键合的氨基酸残基或至少具有两个氨基酸残基的肽；其中R.sup.1为C.sub.5-C.sub.13烷基、芳基、芳基烷基、芳基烷基（低碳基）醚或C.sub.5-C.sub.13烷基（低碳基）醚。
• Facile one-pot transformation of 2,3-epoxy alcohols into allylic alcohols: first total synthesis of (−)-4-O-(6′-hydroxy-7′(9′)-dehydro-6′,7′-dihydrogeranyl)coniferol
  作者：Zuosheng Liu、Jiong Lan、Yulin Li

  DOI：10.1016/s0957-4166(98)00385-1

  日期：1998.11

  An efficient and practical synthesis of optically active allylic alcohols from 2,3-epoxy alcohols by the in situ formation of the epoxy iodides and their subsequent reduction with phosphine hydroxyiodide has been established. Using this reaction as the key step, we synthesized (-)-4-O-(6'-hydroxy-7'(9')-dehydro-6',7'-dihydrogeranyl)coniferol. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Heteroatom-Assisted Isomerization of Oxiranes to Allylic Alcohols Promoted by Bases
  作者：Alessandro Mordini、Sabina Pecchi、Giuseppe Capozzi、Antonella Capperucci、Alessandro Degl'Innocenti、Gianna Reginato、Alfredo Ricci

  DOI：10.1021/jo00096a020

  日期：1994.8

  The isomerization of alkoxy-substituted oxiranes to hydroxy-substituted ene ethers promoted by mixed metal bases has been investigated. The structure of the oxirane substrate (the number, the position, and the type of alkyl substituents on the ring) plays an important role in driving the stereoselectivity of the reaction. Disubstituted oxiranes show a predictable preference for the E-ene ether while trisubstituted substrates give either a mixture of stereoisomers or the E-ene ether exclusively, depending on the location of the third alkyl substituent.