1-benzyloxy-3-iodo-2-propanol | 148218-92-2

• 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: 1-benzyloxy-3-iodo-2-propanol
• 英文别名: 3-O-Benzylglycerin-1-iodhydrin；1-Iodo-3-phenylmethoxypropan-2-ol
• CAS: 148218-92-2
• 化学式: C₁₀H₁₃IO₂
• 分子量: 292.117
• InChiKey: FTFXUOBCQQONHE-UHFFFAOYSA-N

物化性质

• 沸点：
  334.3±37.0 °C(Predicted)
• 密度：
  1.637±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyloxy-3-iodo-2-propanol 在 三乙基硼 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 77.0h， 生成 (+/-)-1-benzyloxy-4-pentyn-2-ol
  参考文献：
  名称：

  The First Radical Method for the Introduction of an Ethynyl Group Using a Silicon Tether and Its Application to the Synthesis of 2‘-Deoxy-2‘-C-ethynylnucleosides¹

  摘要：

  A novel radical method for the stereoselective introduction of an ethynyl group has been developed. When a solution of ethynyldimethylsilyl (EDMS) or [2-(trimethylsilyl)ethynyl]dimethylsilyl (TEDMS) ethers of trans-2-iodoindanol was treated with Et3B followed by tetrabutylammonium fluoride in toluene, atom transfer 5-exo-cyclization and subsequent elimination occurred to give cis-2-ethynylindanol in high yield. The method was shown to be useful in the introduction of an ethynyl group in various five- and six-membered-ring iodohydrins. Furthermore, 2'-deoxy-2'-C-ethynyl-uridine (6) and -cytidine (7), which were designed as novel antimetabolites, were readily synthesized by using this method as the key step. This would be the first example in which a radical reaction was used for introducing an ethynyl group.

  DOI：

  10.1021/jo0206667
• 作为产物：
  描述：

  苄基缩水甘油醚 在 lithium iodide 、 1-hexyl-3-methylimidazolium perchlorate 作用下， 反应 1.0h， 以93%的产率得到1-benzyloxy-3-iodo-2-propanol
  参考文献：
  名称：

  离子液体中金属卤化物在 1,2-环氧化物开环反应中的“金属离子亲电催化”

  摘要：

  金属离子亲电催化 (Li + > Na + K + ) 已在离子液体中金属卤化物 MHal 对 1,2-环氧化物 1-5 的开环反应中发现。结果已基于过渡态合理化，其中阳离子 M + 稳定环氧乙烷环氧原子上产生的负电荷，同时有利于离子对阴离子 Hal - 对相邻碳的亲核攻击。

  DOI：

  10.1055/s-2006-941562

文献信息

• Samarium(III) Iodide ComplexCatalyzed Regioselective Cleavage of Epoxides to Iodohydrins:Tandem Epoxide Opening-Iodocyclization
  作者：Yong Hae Kim、Doo Won Kwon、Min Seok Cho

  DOI：10.1055/s-2003-39310

  日期：——

  A novel tandem iodocyclization has been achieved by the regioselective ring-opening of epoxide and by the following intramolecular 1,4-cycloaddition of α,β-unsaturated ester with catalytic amount of SmI2 and I2 (1.2-2.5 equivalent) under mild and neutral reaction conditions.

  在温和的中性反应条件下，通过环氧化物的区域选择性开环，以及随后在催化量 SmI2 和 I2（1.2-2.5 当量）的作用下对δ,δ-不饱和酯进行分子内 1,4-环加成，实现了一种新型串联碘环化反应。
• An Efficient and Convenient Protocol for Highly Regioselective Cleavage of Terminal Epoxides to β-Halohydrins
  作者：Bu-Bing Zeng、Tao Wang、Wen-Hao Ji、Zhong-Yu Xu

  DOI：10.1055/s-0029-1217182

  日期：——

  An efficient and facile strategy for the cleavage of terminal epoxides to β-halohydrins using active magnesium halides is described. The conversion proceeds smoothly at room temperature with high regioselectivity and good yields even when sensitive functional groups are present.

  描述了使用活性卤化镁将末端环氧化物裂解为 β-卤代醇的有效且简便的策略。转化在室温下顺利进行，具有高区域选择性和良好的产率，即使存在敏感的官能团。
• Tandem SN2-Michael addition to vinylogous carbonates for the stereoselective construction of 2,3,3,5-tetrasubstituted tetrahydrofurans
  作者：Santosh J. Gharpure、S. Raja Bhushan Reddy

  DOI：10.1016/j.tetlet.2010.09.008

  日期：2010.11

  A stereoselective method for the synthesis of substituted tetrahydrofuran derivatives employing a tandem alkylation-Michael addition sequence to vinylogous carbonates is developed. The method could be used to synthesize THFs bearing tertiary ethers. Further, the method is extended to the synthesis of adjacent bis-THFs. (C) 2010 Elsevier Ltd. All rights reserved.