trans-Dimethyl-β-styrolborat | 60806-01-1

• 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: trans-Dimethyl-β-styrolborat
• 英文别名: dimethoxy-[(E)-2-phenylethenyl]borane
• CAS: 60806-01-1
• 化学式: C₁₀H₁₃BO₂
• 分子量: 176.023
• InChiKey: IYHCYMSUONWPTC-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-Dimethyl-β-styrolborat 、 反式-查耳酮 在 (R)-3,3'-bisiodo-1,1'-binaphthalen-2,2'-diol 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以97%的产率得到(S,E)-1,3,5-triphenyl-pent-4-en-1-one
  参考文献：
  名称：

  Asymmetric Conjugate Alkenylation of Enones Catalyzed by Chiral Diols

  摘要：

  Reaction of dimethyl alkenylboronates with alpha,beta-unsaturated ketones in the presence of catalytic amounts of 3,3'-disubstituted binaphthols provides conjugate alkenylation products in good yields and with generally high (similar to 99:1 er) stereoselectivities.

  DOI：

  10.1021/ja0713734

文献信息

• Synthesis of Optically Active N-Aryl Amino Acid Derivatives through the Asymmetric Petasis Reaction Catalyzed by a Novel Hydroxy-Thiourea Catalyst
  作者：Tsubasa Inokuma、Yusuke Suzuki、Toshiyuki Sakaeda、Yoshiji Takemoto

  DOI：10.1002/asia.201100453

  日期：2011.11.4

  vinylboronates and α‐iminoamides are effectively catalyzed by the novel hydroxy–thiourea catalyst 1 (up to 86 % yield, 93 % ee; see scheme). This reaction can be applied not only to the synthesis of the unnatural amino acid monomers but also to peptide oligomers.

  硫脲制造肽：新型羟基-硫脲催化剂1可有效催化乙烯基硼酸酯和α-亚氨基酰胺的不对称Petasis反应（产率高达86％，ee为93％；参见方案）。该反应不仅可以用于非天然氨基酸单体的合成，而且可以应用于肽低聚物。
• Asymmetric Petasis Reactions Catalyzed by Chiral Biphenols
  作者：Sha Lou、Scott E. Schaus

  DOI：10.1021/ja8018934

  日期：2008.6.1

  Chiral biphenols catalyze the enantioselective Petasis reaction of alkenyl boronates, secondary amines, and ethyl glyoxylate. The reaction requires the use of 15 mol % of (S)-VAPOL as the catalyst, alkenyl boronates as nucleophiles, ethyl glyoxylate as the aldehyde component, and 3 A molecular sieves as an additive. The chiral alpha-amino ester products are obtained in good yields (71-92%) and high

  手性双酚催化烯基硼酸酯、仲胺和乙醛酸乙酯的对映选择性 Petasis 反应。该反应需要使用15mol%的(S)-VAPOL作为催化剂，硼酸烯基作为亲核试剂，乙醛酸乙酯作为醛组分，3A分子筛作为添加剂。以良好的产率 (71-92%) 和高对映体比率 (89:11-98:2) 获得手性 α-氨基酯产物。机理研究表明无环硼酸酯与 VAPOL 和四配位硼酸酯中间体的单配体交换。
• Asymmetric Conjugate Alkenylation of Enones Catalyzed by Chiral Diols
  作者：T. Robert Wu、J. Michael Chong

  DOI：10.1021/ja0713734

  日期：2007.4.1

  Reaction of dimethyl alkenylboronates with alpha,beta-unsaturated ketones in the presence of catalytic amounts of 3,3'-disubstituted binaphthols provides conjugate alkenylation products in good yields and with generally high (similar to 99:1 er) stereoselectivities.