1-[1-[1-hydroxy-2-phenylcarbonyloxy-(1R)-ethyl]-(1S)-3-butenyloxymethyl]benzene | 344341-14-6

• 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-[1-[1-hydroxy-2-phenylcarbonyloxy-(1R)-ethyl]-(1S)-3-butenyloxymethyl]benzene
• 英文别名: benzoic acid 3-benzyloxy-2-hydroxy-hex-5-enyl ester；[(2R,3S)-2-hydroxy-3-phenylmethoxyhex-5-enyl] benzoate
• CAS: 344341-14-6
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: JPLFJCKMUSCBPL-MOPGFXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[1-[1-hydroxy-2-phenylcarbonyloxy-(1R)-ethyl]-(1S)-3-butenyloxymethyl]benzene 在 三乙基硅烷 、 三氟化硼乙醚 、 氧气 、 copper(l) chloride 、 palladium dichloride 作用下， 以 水 、 乙腈 为溶剂， 反应 2.25h， 生成 3-benzyloxy-5-methyl-2-phenylcarbonyloxymethyl-(2R,3S)-tetrahydrofuran
  参考文献：
  名称：

  Pd(II)-mediated synthesis of 2-deoxy- and rare-C-glycosides

  摘要：

  The synthesis of 2-deoxy-C-glycosides and rare-C-saccharides from the gamma,delta -olefinic alcohols is described. In the presence of Pd(II) reagents these olefinic alcohols undergo an efficient intramolecular oxidative cyclisation to afford the target molecules. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00098-2
• 作为产物：
  描述：

  (R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane 在 吡啶 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 1-[1-[1-hydroxy-2-phenylcarbonyloxy-(1R)-ethyl]-(1S)-3-butenyloxymethyl]benzene
  参考文献：
  名称：

  Pd(II)-mediated synthesis of 2-deoxy- and rare-C-glycosides

  摘要：

  The synthesis of 2-deoxy-C-glycosides and rare-C-saccharides from the gamma,delta -olefinic alcohols is described. In the presence of Pd(II) reagents these olefinic alcohols undergo an efficient intramolecular oxidative cyclisation to afford the target molecules. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00098-2

文献信息

• Retro-Claisen Condensation with FeIII as Catalyst under Solvent-Free Conditions
  作者：Chitturi Bhujanga Rao、Dasireddi Chandra Rao、Dokuburra Chanti Babu、Yenamandra Venkateswarlu

  DOI：10.1002/ejoc.201000140

  日期：2010.5

  An iron(III) salt catalyzed retro-Claisen condensation between an alcohol and a 1,3-diketone was investigated. The mechanism involves the formation of a metal-induced six-membered cyclic transition state and cleavage of the C–C bond. Regioselective esterification and one-pot conversion of silyl ethers into esters with good yields was observed. Simple reaction conditions, high yields, and broad scope

  研究了铁 (III) 盐催化醇和 1,3-二酮之间的逆克莱森缩合反应。该机制涉及金属诱导的六元环状过渡态的形成和 C-C 键的断裂。观察到区域选择性酯化和甲硅烷基醚以良好产率一锅法转化为酯。反应条件简单，收率高，反应范围广，说明该方法具有良好的合成实用性。
• Pd(II)-mediated synthesis of 2-deoxy- and rare-C-glycosides
  作者：G.V.M. Sharma、A.Subhash Chander、Palakodety Radha Krishna

  DOI：10.1016/s0957-4166(01)00098-2

  日期：2001.3

  The synthesis of 2-deoxy-C-glycosides and rare-C-saccharides from the gamma,delta -olefinic alcohols is described. In the presence of Pd(II) reagents these olefinic alcohols undergo an efficient intramolecular oxidative cyclisation to afford the target molecules. (C) 2001 Elsevier Science Ltd. All rights reserved.