3-hydroxy-3-phenylpropyltriphenylphosphonium bromide | 137003-82-8

• 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: 3-hydroxy-3-phenylpropyltriphenylphosphonium bromide
• 英文别名: Phosphonium, (3-hydroxy-3-phenylpropyl)triphenyl-, bromide；(3-hydroxy-3-phenylpropyl)-triphenylphosphanium;bromide
• CAS: 137003-82-8
• 化学式: Br*C₂₇H₂₆OP
• 分子量: 477.381
• InChiKey: BODQXHWNFLAMLA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-3-phenylpropyltriphenylphosphonium bromide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 trans-4-formyl-2-phenyl-tetrahydropyran
  参考文献：
  名称：

  从 3-和 4-羟基烷基鏻盐合成环醚

  摘要：

  在 N,N-二异丙基乙胺存在下，由 3-羟烷基三苯基鏻盐和多聚甲醛衍生的 6-亚甲基-1,3-二氧杂环己烷与三氟甲磺酸三甲基甲硅烷基酯反应生成新型 4-甲酰基四氢吡喃。3-亚甲基四氢吡喃是通过 4-羟基烷基三苯基碘化鏻与 DBU 和多聚甲醛反应合成的。2,3-二氢-3-亚甲基苯并呋喃也可通过 2-羟基苄基三苯基溴化鏻与丁基锂反应，然后加入多聚甲醛获得。

  DOI：

  10.1246/bcsj.78.2209
• 作为产物：
  描述：

  氧化苯乙烯 、 亚甲基三苯基膦烷 生成 3-hydroxy-3-phenylpropyltriphenylphosphonium bromide
  参考文献：
  名称：

  Novel Synthesis of Methylenecyclobutanols and 4-Methylenetetrahydrofurans from γ-Oxide Ylides

  摘要：

  The reaction of partial derivative-halo-gamma-oxide ylide, prepared from methylenetriphenylphosphorane and epichlorohydrin, with aldehydes afforded alkylidenecyclobutanols in moderate yields. The reaction initially proceeded through internal nucleophilic attack on partial derivative-carbon of this ylide. Another novel approach toward the synthesis of 4-methylenetetrahydrofurans was achieved by the reaction of gamma-oxide ylides with paraformaldehyde.

  DOI：

  10.1021/jo0202435

文献信息

• Photoinduced Alcoholic α‐C−H Bond Anti‐Markovnikov Addition to Vinylphosphonium Bromides Followed by Wittig Olefination: Two‐Step Protocol for α‐C−H Allylic Alkylation of Alcohols
  作者：Masaki Yoshida、Masaya Sawamura、Yusuke Masuda

  DOI：10.1002/cctc.202200744

  日期：2022.9.20

  Photocatalytic Synthesis: A two-step protocol for the α-allylic alkylation of alcohols consisting of photocatalytic anti-Markovnikov addition of the α-C−H bond of alcohols to vinylphosphonium bromides and subsequent Wittig olefination with aldehydes is reported. The protocol is marked by simplicity of the photoreaction system with a single catalyst and broad scope of alcohols, ranging from readily

  光催化合成：报告了醇的 α-烯丙基烷基化的两步方案，该方案由醇的 α-C-H 键光催化反马尔科夫尼科夫加成到乙烯基溴化鏻和随后与醛的 Wittig 烯化组成。该协议的特点是光反应系统的简单性，具有单一催化剂和广泛的醇类，从现成的化学原料到功能化分子。
• Bestmann, Hans Juergen; Riemer, Claus; Doetzer, Reinhard, Chemische Berichte, 1992, vol. 125, # 1, p. 225 - 229
  作者：Bestmann, Hans Juergen、Riemer, Claus、Doetzer, Reinhard

  DOI：——

  日期：——
• Novel Synthesis of Methylenecyclobutanols and 4-Methylenetetrahydrofurans from γ-Oxide Ylides
  作者：Kentaro Okuma、Yoshihiro Kamahori、Kimiko Tsubakihara、Kanami Yoshihara、Yuichiro Tanaka、Kosei Shioji

  DOI：10.1021/jo0202435

  日期：2002.10.1

  The reaction of partial derivative-halo-gamma-oxide ylide, prepared from methylenetriphenylphosphorane and epichlorohydrin, with aldehydes afforded alkylidenecyclobutanols in moderate yields. The reaction initially proceeded through internal nucleophilic attack on partial derivative-carbon of this ylide. Another novel approach toward the synthesis of 4-methylenetetrahydrofurans was achieved by the reaction of gamma-oxide ylides with paraformaldehyde.
• Synthesis of Cyclic Ethers from 3- and 4-Hydroxyalkylphosphonium Salts
  作者：Kentaro Okuma、Osami Sakai、Tetsuji Hayano、Kosei Shioji、Haruo Matsuyama

  DOI：10.1246/bcsj.78.2209

  日期：2005.12

  The reaction of 6-methylene-l,3-dioxepanes derived from 3-hydroxyalkyltriphenylphosphonium salts and paraformaldehyde with trimethylsilyl trifluoromethanesulfonate in the presence of N,N-diisopropylethylamine yielded novel 4-formyltetrahydropyrans. 3-Methylenetetrahydropyrans were synthesized by the reaction of 4-hydroxyalkyltriphenyl-phosphonium iodides with DBU and paraformaldehyde. 2,3-Dihydro-

  在 N,N-二异丙基乙胺存在下，由 3-羟烷基三苯基鏻盐和多聚甲醛衍生的 6-亚甲基-1,3-二氧杂环己烷与三氟甲磺酸三甲基甲硅烷基酯反应生成新型 4-甲酰基四氢吡喃。3-亚甲基四氢吡喃是通过 4-羟基烷基三苯基碘化鏻与 DBU 和多聚甲醛反应合成的。2,3-二氢-3-亚甲基苯并呋喃也可通过 2-羟基苄基三苯基溴化鏻与丁基锂反应，然后加入多聚甲醛获得。