2,2-Dimethyl-propionic acid (S)-4-hydroxy-4-phenyl-butyl ester | 139527-17-6

• 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: 2,2-Dimethyl-propionic acid (S)-4-hydroxy-4-phenyl-butyl ester
• 英文别名: [(4S)-4-hydroxy-4-phenylbutyl] 2,2-dimethylpropanoate
• CAS: 139527-17-6
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: MTIJAAWWQNORSE-ZDUSSCGKSA-N

物化性质

• 沸点：
  365.6±35.0 °C(Predicted)
• 密度：
  1.044±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲醛 、 di(3-pivaloyloxypropyl)zinc 在 titanium(IV) isopropylate 、 bis((trimethylsilyl)methyl)zinc 、 (1R)-反-N,N′-1,2-环己二基双(1,1,1-三氟甲磺酰胺) 作用下， 以 乙醚 为溶剂， 以81%的产率得到2,2-Dimethyl-propionic acid (S)-4-hydroxy-4-phenyl-butyl ester
  参考文献：
  名称：

  Highly Enantioselective Addition of Mixed Diorganozincs to Aldehydes^†

  摘要：

  DOI：

  10.1021/jo971488y

文献信息

• Neopentyl and Neophyl Groups: New Nontransferable Groups for Organocopper and Organozinc Chemistry
  作者：Christian Lutz、Philip Jones、Paul Knochel

  DOI：10.1055/s-1999-3387

  日期：1999.2

  Neopentyl and Neophyl groups have been found to be excellent nontransferable groups for organozinc and organocopper chemistry. We have shown that mixed diorganozincs of the type FG-R-Zn(CH2CMe2R) can be used advantageously for the enantioselective addition to aldehydes. These mixed copper or zinc reagents are also found to be very efficient in the Michael addition to various activated alkenes.

  研究发现，新戊基和新苯基是一类优良的非转移性基团，适用于有机锌和有机铜化学。我们已经证明，类型为 FG-R-Zn(CH2CMe2R) 的混合二有机锌可以用于对醛的对映选择性加成。这些混合铜或锌试剂在向各种活化烯烃的迈克尔加成中也表现出非常高的效率。
• Catalytic asymmetric reductive addition of olefins to aldehydes mediated by boron and zinc organometallics
  作者：Lothar Schwink、Paul Knochel

  DOI：10.1016/0040-4039(94)88412-9

  日期：1994.11

  A procedure involving a hydroboration, boron-zinc exchange and asymmetric addition to an aldehyde allows the reductive addition of olefins to aldehydes in 50–96 % ee. A short and efficient 3 step synthesis of ginnol (61 % overall yield, 92 % ee) demonstrates the synthetic utility of the method.

  涉及硼氢化反应，硼锌交换和不对称加成醛的过程，可以使烯烃以50–96％ee还原性加成到醛中。短而有效的三步合成ginnol（61％的总收率，92％ee）证明了该方法的合成效用。
• Preparation of Functionalized Dialkylzincs via a Boron−Zinc Exchange. Reactivity and Catalytic Asymmetric Addition to Aldehydes
  作者：Falk Langer、Lothar Schwink、Arokiasamy Devasagayaraj、Pierre-Yves Chavant、Paul Knochel

  DOI：10.1021/jo961129n

  日期：1996.11.15

  The hydroboration of olefins with Et(2)BH provides diethyl(alkyl)boranes 2 which readily undergo a boron-zinc exchange with Et(2)Zn providing a range of polyfunctional primary, secondary, and benzylic diorganozincs. The resulting diorganozincs 3 have been reacted with various electrophiles (allylic halides, acid chlorides, alkylidenemalonates, ethyl propiolate, nitroolefins) in the presence of CuCN

  烯烃与Et（2）BH的氢硼化反应生成的二乙基（烷基）硼烷2容易与Et（2）Zn进行硼-锌交换，从而提供了一系列多官能的伯，仲和苄基二有机锌。在CuCN.2LiCl存在下，使所得的二有机锌3与各种亲电试剂（烯丙基卤化物，酰氯，亚烷基丙二酸酯，丙酸乙酯，硝基烯烃）反应，具有极好的收率。用由非对映体纯的二乙基（烷基）硼烷制备的仲二烷基锌，发生硼-锌交换而失去立体化学。在手性催化剂55的存在下，将3-不对称地加成到醛中，提供了光学活性的多官能仲醇（50至超过96％ee）。
• Preparation of functionalized dialkylzinc reagents via an iodine-zinc exchange reaction. Highly enantioselective synthesis of functionalized secondary alcohols
  作者：Michael J. Rozema、AchyuthaRao Sidduri、Paul Knochel

  DOI：10.1021/jo00033a008

  日期：1992.3

  Functionalized dialkylzincs are obtained by the reaction of polyfunctional alkyl iodides with Et2Zn in excellent yield. Their treatment with aldehydes, in the presence of the titanium catalyst 6, affords functionalized secondary alcohols with high enantioselectivity.