bis(5-acetoxypentyl)zinc | 139527-23-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: bis(5-acetoxypentyl)zinc
• CAS: 139527-23-4
• 化学式: C₁₄H₂₆O₄Zn
• 分子量: 323.748
• InChiKey: VHSOBJFNEMRBEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis(5-acetoxypentyl)zinc 在 (1R)-反-N,N′-1,2-环己二基双(1,1,1-三氟甲磺酰胺) titanium(IV) isopropylate 作用下， 反应 0.17h， 生成 Acetic acid (S)-6-(tert-butyl-diphenyl-silanyloxy)-8-oxo-octyl ester
  参考文献：
  名称：

  A new catalytic asymmetric approach to polyfunctional aldol products mediated by zinc organometallics

  摘要：

  The catalytic asymmetric addition of functionalized dialkylzincs to beta-alkoxyaldehydes provides after a short sequence of functional group interconversions aldol products in 40-99% ee. Their stereoselective transformation to either syn- or anti-1,3-diols has been performed.

  DOI：

  10.1016/s0040-4039(00)73804-4
• 作为产物：
  描述：

  5-iodopentyl acetate 、 diethylzinc 以80%的产率得到
  参考文献：
  名称：

  Ostwald Roswitha, Chavant Pierre-Yves, Stadtmueller Heinz, Knochel Paul, J. Org. Chem., 59 (1994) N 15, S 4143-4153

  摘要：

  DOI：

文献信息

• New Efficient Nickel-Catalyzed Cross-Coupling Reaction between Two Csp³ Centers
  作者：Riccardo Giovannini、Thomas Stüdemann、Arokiasamy Devasagayaraj、Gaëlle Dussin、Paul Knochel

  DOI：10.1021/jo982317b

  日期：1999.5.1

  carbonyl group, cyano group) in an alkyl halide facilitates its cross-coupling reaction with various diorganozincs in the presence of Ni(acac)(2) (7.5-10 mol % in THF/NMP mixtures). These results were used to develop a new general cross-coupling reaction between functionalized diorganozincs and alkyl iodides using m- or p-trifluoromethylstyrene as a reaction promotor and Ni(acac)(2) as a catalyst (7.5-10

  在Ni（acac）（2）（在THF / NMP中为7.5-10 mol％）的情况下，卤代烷中存在不饱和键（双键，羰基，氰基）有助于其与各种二有机锌的交叉偶联反应混合物）。这些结果被用来开发新的一般的功能化二有机锌和烷基碘之间的交叉偶联反应，使用间或对三氟甲基苯乙烯作为反应促进剂，并使用Ni（acac）（2）作为催化剂（7.5-10 mol％；-35 ℃，5-10 h）导致了广泛的多功能交叉偶联产品。
• Peptidic Amidomonophosphane Ligand for Copper-Catalyzed Asymmetric Conjugate Addition of Diorganozincs to Cycloalkenones
  作者：Takahiro Soeta、Khalid Selim、Masami Kuriyama、Kiyoshi Tomioka

  DOI：10.1002/adsc.200600562

  日期：2007.3.5

  pyrrolidine gave a dipeptide-connected amidomonophosphane ligand for the highly efficient, copper-catalyzed asymmetric conjugate addition reaction of organozinc reagents with cycloalkenones, giving 3-alkylated cycloalkanones in high enantioselectivity of up to 98 % ee. A model that predicts the stereochemistry of the reaction is discussed.

  （S）-2-[（（二苯基膦基）甲基]吡咯烷的肽基修饰为有机锌试剂与环烯酮的高效铜催化不对称共轭加成反应提供了一个二肽连接的酰胺基单膦配体，从而在高对映体选择性下得到了3-烷基化的环烷酮ee高达98％。讨论了预测反应立体化学的模型。
• New Chiral Oxazoline-Phosphite Ligands for the Enantioselective Copper-Catalyzed 1,4-Addition of Organozinc Reagents to Enones
  作者：Iris H Escher、Andreas Pfaltz

  DOI：10.1016/s0040-4020(00)00143-5

  日期：2000.4

  A series of new P,N-ligands with a binaphthyl and an oxazoline moiety were prepared, which are efficient ligands for the enantioselective copper-catalyzed 1,4-addition of organozinc reagents to enones. Increasing the steric bulk in the 3,3′-position of binaphthyl from an H to a biphenylyl moiety improved the ee from 65 to 94% in the reaction of diethylzinc with cyclopentenone.

  制备了一系列具有联萘基和恶唑啉部分的新的P，N-配体，它们是对映选择性铜催化的有机锌试剂向烯酮的1,4-加成反应的有效配体。在二乙基锌与环戊烯酮的反应中，将联萘的3,3'-位的空间体积从H增加到联苯基部分，可将ee从65％提高到94％。
• Stadtmüller, Heinz; Knochel, Paul, Organometallics, 1995, vol. 14, # 7, p. 3163 - 3166
  作者：Stadtmüller, Heinz、Knochel, Paul

  DOI：——

  日期：——
• New strategy for the preparation of nitrogen- and phosphorus-containing chiral polyfunctional secondary alcohols
  作者：Christian Lutz、Claus-Dieter Graf、Paul Knochel

  DOI：10.1016/s0040-4020(98)00487-6

  日期：1998.8

  The use of borane-derived protecting groups for aldehydes containing pyridine and phosphine functionalities allows the performance of highly enantioselective additions of functionalized diorganizincs leading to polyfunctional chiral hydroxy-pyridines and -phosphines with excellent enantioselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.