2,2'-(2-phenyl-ethene-1,1-diyl)-bis-benzo[1,3,2]dioxaborole | 26071-86-3

• 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: 2,2'-(2-phenyl-ethene-1,1-diyl)-bis-benzo[1,3,2]dioxaborole
• 英文别名: 2-Phenylaethen-1,1-diborsaeurecatecholester
• CAS: 26071-86-3
• 化学式: C₂₀H₁₄B₂O₄
• 分子量: 339.951
• InChiKey: SURNESRFUCDPQH-UHFFFAOYSA-N

物化性质

• 沸点：
  462.3±55.0 °C(predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  tetrakis(dimethoxyboryl)methane 、 苯甲醛 、 邻苯二酚 生成 2,2'-(2-phenyl-ethene-1,1-diyl)-bis-benzo[1,3,2]dioxaborole
  参考文献：
  名称：

  三甲基溴化物阴离子与酮或醛的缩合反应生成的1,1-二硼烷烯烃酯

  摘要：

  的triborylmethide离子，[（RO）2 B] 3 Ç - ，从甲基锂与methanetetraboronic酸的甲基酯，C [B（OME）的反应2 ] 4，或频哪醇酯，C（BO 2 ç 2我4）4，冷凝很容易地用酮，R' 2 CO，以形成烯烃-1,1-二硼酸的酯，R' 2 CC[B（OR）2 ] 2。该反应是一般反应，并且可以耐受其他官能团，包括α-氯，乙氧基和叔氨基取代基。乙醛和苯甲醛也发生缩合。烯烃-1，1-二硼酸酯是潜在有用的合成中间体。它们的反应包括通过过氧化氢转化为羧酸，通过溴转化为α-溴代烯烃硼酸酯，以及通过氯化汞和乙酸钠转化为烯基-1,1-二汞氯化物。

  DOI：

  10.1016/s0022-328x(00)92985-1

文献信息

• Rhodium(I) catalysed diboration of (E)-styrylboronate esters: molecular structures of (E)-p-MeO–C6H4–CHCH–B(1,2-O2C6H4) and p-MeO–C6H4–CH2C{B(1,2-O2C6H4)}3
  作者：Paul Nguyen、R.Benjamin Coapes、Alden D Woodward、Nicholas J Taylor、Jacquelyn M Burke、Judith A.K Howard、Todd B Marder

  DOI：10.1016/s0022-328x(02)01310-4

  日期：2002.6

  Diboration of the styrylboronate esters (E)-p-R-C6H4-CH=CH-Bcat (1) (R = H, (1a) MeO (1b); cat = 1,2-O2C6H4), with B(2)cat(2) in the presence of a variety of rhodium phosphine catalysts gives predominantly either p-R-C6H4-CH2C(Bcat)(3)), (2), which contains three boronate ester groups on one carbon atom, or its isomer p-R-C6H4-CH(Bcat)CH(Bcat)(2) (3). The formation of 2 apparently involves regiospecific insertion of the vinylboronates into a Rh-B bond followed by P-hydride elimination, another regiospecific insertion of the 2,2-vinyl bis(boronate) into the remaining Rh-B bond followed by C-H reductive elimination leading to 2,2-diboration and a 2.1-hydrogen shift. Wilkinson's catalyst (7) gives the highest yields of 2 with 75 and 71% yields from la and 1b, respectively, while [Rh(COE)(2)(mu-Cl)](2) (10) with two equivalents of P(o-tol)(3) gave 3 in highest yield with 50 and 49% from 1a and 1b, respectively. The crystal structure of (E)-p-MeO-C6H4-CH=CH-Bcat shows the molecule to be essentially planar. with the phenyl ring twisted slightly out of the plane. The tris(boronate) p-MeO-C6H4-CH2C(Bcat)(3) crystallises with two independent molecules in the unit cell, which differ in the rotational orientation of the phenyl ring in relation to the catecholate groups: the latter are arranged in a propeller-like fashion. (C) 2002 Elsevier Science B.V. All rights reserved.