cis-3,cis-4-bis(benzyloxymethyl)-1,2-epoxycyclobutane | 161511-13-3

• 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: cis-3,cis-4-bis(benzyloxymethyl)-1,2-epoxycyclobutane
• 英文别名: (1S,2R,3S,4R)-2,3-bis(phenylmethoxymethyl)-5-oxabicyclo[2.1.0]pentane
• CAS: 161511-13-3
• 化学式: C₂₀H₂₂O₃
• 分子量: 310.393
• InChiKey: YEXCCZQZQXHKRH-FGYAAKKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  cis-3,cis-4-bis(benzyloxymethyl)-1,2-epoxycyclobutane 在 sodium hydroxide 、 sodium tetrahydroborate 、 氢溴酸 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 Methanesulfonic acid (1S,2R,3S)-2,3-bis-benzyloxymethyl-cyclopropylmethyl ester
  参考文献：
  名称：

  新型环丙烷碳环核苷关键步骤中涉及C 4 -C 3环收缩的制备

  摘要：

  顺式3，4-双（苄氧基甲基）环丁-1-烯1主要导致溴代醇5，其在溴和苄氧基甲基之间具有顺式关系。5的立体有择环收缩提供醛7，可以将其转化为核苷类似物1 2。

  DOI：

  10.1016/0040-4039(95)01536-1
• 作为产物：
  描述：

  cis-3-cyclobutene-1,2-dimethanol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.25h， 生成 cis-3,cis-4-bis(benzyloxymethyl)-1,2-epoxycyclobutane 、 trans-3,trans-4-bis(benzyloxymethyl)-1,2-epoxycyclobutane
  参考文献：
  名称：

  Novel cyclobutane carbocyclic nucleosides

  摘要：

  Epoxidation of cis-3,4-bis(benzyloxymethyl)cyclobut-1-ene 4 gave compounds 7a and 7b which were separated Reaction of the cis-epoxide 7a with adenine led to the N-9 and N-7 attack products, 10a and 10b, respectively. In the same conditions, the trans-epoxide 7b yielded the N-9 product 12. Nucleoside analogues 11 and 13 were obtained by debenzylation of 10a and 12, respectively.

  DOI：

  10.1016/s0040-4020(01)89324-8

文献信息

• Synthesis of a novel trisubstituted cyclobutane nucleoside analogue. Unexpected C4-C3 ring contractions in related reactions
  作者：Laurence Mévellec、François Huet

  DOI：10.1016/s0040-4020(97)00266-4

  日期：1997.4

  mesylate 5b. On the other hand the same reaction starting from its isomer 5a did not work and led to the surprising ring contraction products 8a and 8b. Another unexpected ring contraction leading to 15 was pointed out in the course of preparation of the deuteriated compounds 5a′ and 5a″. Position of deuterium in products 8a′ and 8b′ or 8a″ and 8b″ issued from reactions with 5a′ or 5a″ gave useful mechanistic

  核苷类似物7是通过腺嘌呤和甲磺酸盐5b之间的亲核取代获得的。另一方面，从其异构体5a开始的相同反应无效，并导致令人惊讶的环收缩产物8a和8b。在制备氘代化合物5a'和5a ''的过程中指出了导致15的另一个意外的环收缩。在产品的氘位置8A'和8B'或图8a“和8b显示”从与反应发出5A'或5A“ 提供了有关该反应的有用的机理信息。
• High selectivities in electrophilic additions to cyclobutene compounds
  作者：Laurence Mévellec、Michel Evers、François Huet

  DOI：10.1016/s0040-4020(96)00945-3

  日期：1996.11

  Epoxidation of 2, 3, 4 with m-CPBA mainly led to the cis-attack products whereas 1 and 6 led to the other selectivity. The result was reversed, from 4, with Payne's reagent Bromohydroxylation of 4 involved an intermediate bromonium ion syn to the substituents. Haloselenylations occurred with the syn-selectivity from 1, 2, 3 and 4, to the anti-selectivity from 6, and without selectivity from 5. NOE enhancement measurements and several chemical correlations led to the stereochemical assignments. Formation of the intramolecular reaction products 24 and 25 was also pointed out. Copyright (C) 1996 Elsevier Science Ltd
• Novel cyclobutane carbocyclic nucleosides
  作者：Laurence Mévellec、François Huet

  DOI：10.1016/s0040-4020(01)89324-8

  日期：1994.1

  Epoxidation of cis-3,4-bis(benzyloxymethyl)cyclobut-1-ene 4 gave compounds 7a and 7b which were separated Reaction of the cis-epoxide 7a with adenine led to the N-9 and N-7 attack products, 10a and 10b, respectively. In the same conditions, the trans-epoxide 7b yielded the N-9 product 12. Nucleoside analogues 11 and 13 were obtained by debenzylation of 10a and 12, respectively.
• Preparation involving a C4-C3 ring contraction in the key step of a novel cyclopropane carbocyclic nucleoside
  作者：Laurence Mévellec、François Huet

  DOI：10.1016/0040-4039(95)01536-1

  日期：1995.10

  Cis-3,4-bis(benzyloxymethyl)cyclobut-1-ene 1 mainly led to bromohydrin 5 with a cis relationship between bromine and the benzyloxymethyl groups. The stereospecific ring contraction of 5 afforded aldehyde 7 which could be converted into the nucleoside analogue 1 2.

  顺式3，4-双（苄氧基甲基）环丁-1-烯1主要导致溴代醇5，其在溴和苄氧基甲基之间具有顺式关系。5的立体有择环收缩提供醛7，可以将其转化为核苷类似物1 2。