5-氧代-7-苯基庚酸 | 32764-94-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 5-氧代-7-苯基庚酸
• 英文名称: 5-oxo-7-phenylheptanoic acid
• 英文别名: 7-phenyl-5-oxoheptanoic acid；5-oxo-7-phenyl-heptanoic acid；5-Oxo-7-phenyl-heptansaeure；5-Keto-7-phenylheptansaeure；5-Oxo-7-phenylheptansaeure
• CAS: 32764-94-6
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: PCIIZINALXTQHE-UHFFFAOYSA-N

物化性质

• 熔点：
  58 °C
• 沸点：
  397.2±17.0 °C(Predicted)
• 密度：
  1.120±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  5-氧代-7-苯基庚酸 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 葡萄糖 作用下， 以 四氢呋喃 、 正己烷 、 水 、 苯 为溶剂， 反应 16.0h， 生成 Acetic acid (S)-5-hydroxy-7-phenyl-heptyl ester
  参考文献：
  名称：

  Baker's yeast reduction of arylalkyl and arylalkenil γ- and δ-keto acids

  摘要：

  gamma- and delta-Lactones 5, 6, 13, 14, 15 and 16 were synthesized via baker's yeast reduction of the corresponding keto acids 3 ,4 and 9-12. The enantioselectivity of the reduction is strongly dependent on the nature of the keto acid: the delta-lactones were always obtained in an ee% higher than the gamma-lactones and ranging from 70% to 100%.

  DOI：

  10.1016/s0040-4020(01)81944-x
• 作为产物：
  描述：

  5-氧代-7-苯基庚酸甲酯 在 lithium hydroxide 、 水 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 5-氧代-7-苯基庚酸
  参考文献：
  名称：

  通过铑催化的烯基异氰酸酯和末端炔烃的 [2+2+2] 环加成反应，对映选择性合成带有季取代立体中心的吲哚里西啶。

  摘要：

  描述了通过铑催化的取代烯基异氰酸酯和末端炔烃的 [2+2+2] 环加成反应，对映选择性合成带有季取代立体中心的吲哚里西啶。该反应使用脂肪族炔烃提供内酰胺产物，而芳基炔烃产生乙烯基酰胺产物。通过亚磷酰胺配体的修饰，两种产物都获得了高水平的对映选择性、区域选择性和产物选择性。

  DOI：

  10.1021/ol800086s

文献信息

• Asymmetric Hydrogenation of Tetrasubstituted Cyclic Enones to Chiral Cycloalkanols with Three Contiguous Stereocenters
  作者：Yun-Ting Liu、Ji-Qiang Chen、Lin-Ping Li、Xin-Yang Shao、Jian-Hua Xie、Qi-Lin Zhou

  DOI：10.1021/acs.orglett.7b01343

  日期：2017.6.16

  A highly efficient iridium-catalyzed asymmetric hydrogenation of tetrasubstituted cyclic enones has been developed for the enantioselective synthesis of chiral cycloalkanols with three contiguous stereocenters. The C═O and C═C bonds of the enone substrates were hydrogenated sequentially in one pot with excellent enantioselectivity (92 to >99% ee) and diastereoselectivity (dr 95:5 to >99:1). The reaction

  已经开发了一种高效的铱催化的四取代环烯酮的不对称氢化反应，用于对映体选择性合成具有三个连续立体中心的手性环烷醇。烯酮底物的C═O和C═C键在一锅中依次氢化，具有优异的对映选择性（92至> 99％ee）和非对映选择性（dr 95：5至> 99：1）。该反应为抗溃疡药罗沙前列醇的所有立体异构体提供了一种实用的方法。
• Development of a convoluted polymeric nanopalladium catalyst: α-alkylation of ketones and ring-opening alkylation of cyclic 1,3-diketones with primary alcohols
  作者：Yoichi M.A. Yamada、Yasuhiro Uozumi

  DOI：10.1016/j.tet.2007.05.071

  日期：2007.8

  A novel solid-phase catalyst of palladium nanoparticles, nano-Pd-V, was prepared from PdCl2 with main-chain viologen polymers via complexation and reduction. This insoluble nanocatalyst nano-Pd-V efficiently promoted α-alkylation of ketones with primary alcohols in the presence of Ba(OH)2·H2O under atmospheric conditions without organic solvents. The nano-Pd-V catalyst was reused without loss of catalytic

  通过PdCl 2与主链紫精聚合物的络合和还原反应，制备了一种新型的钯纳米颗粒固相催化剂：Nano-Pd-V 。在不存在有机溶剂的大气条件下，在Ba（OH）2 ·H 2 O的存在下，这种不溶的纳米催化剂纳米Pd-V有效地促进了伯醇与酮的α-烷基化。纳米Pd-V催化剂可以重复使用而不会损失催化活性。纳米Pd-V催化剂还催化了环1,3-二酮与伯醇的开环烷基化反应。
• Asymmetric synthesis of spiro 2-pyrrolidin-5-ones and 2-piperidin-6-ones
  作者：Abood A. Bahajaj、Patrick D. Bailey、Madeleine H. Moore、Keith M. Morgan、John M. Vernon

  DOI：10.1039/c39940002511

  日期：——

  Bicyclic lactams 14–17 are isomerised on treatment with aluminium trichloride in 1,2-dichloroethane to give spiro lactams in high yield and >3: 1 diastereoselectivity; from the structures of 19a and 22b determined by X-ray crystallography, it follows that the indenes 19 and 21 are formed preferentially with retention of configuration at the spiro carbon atom and the naphthalenes 20 and 22 with inversion.

  双环内酰胺14-17在三氯化铝处理下于1,2-二氯乙烷中进行异构化，以高产率（>3:1）的非对映选择性生成螺内酰胺；由X射线晶体学确定的结构19a和22b可知，优先形成的是在螺碳原子上保持构型的茚19和21，以及构型翻转的萘20和22。
• Stereoselective synthesis of chiral δ-lactones <i>via</i> an engineered carbonyl reductase
  作者：Tao Wang、Xiao-Yan Zhang、Yu-Cong Zheng、Yun-Peng Bai

  DOI：10.1039/d1cc04542c

  日期：——

  A carbonyl reductase variant, SmCRM5, from Serratia marcescens was obtained through structure-guided directed evolution. The variant showed improved specific activity (U mg−1) towards most of the 16 tested substrates and gave high stereoselectivities of up to 99% in the asymmetric synthesis of 13 γ-/δ-lactones. In particular, SmCRM5 showed a 13.8-fold higher specific activity towards the model substrate

  来自粘质沙雷氏菌的羰基还原酶变体Sm CR M5是通过结构引导的定向进化获得的。该变体对 16 种测试底物中的大多数表现出改善的比活性 (U mg -1 )，并在 13 种 γ-/δ-内酯的不对称合成中提供高达 99% 的高立体选择性。特别是，SmCR M5对模型底物（即5-氧代癸酸）的比活性高出 13.8 倍，并在 99% ee 中产生 ( R )-δ-癸内酯，时空产率 (STY) 为 301 g L -1 d -1. 六种δ-内酯的高收率和高对映体纯度的制备表明这些高附加值化学品的生物催化合成是可行的，为贵金属催化提供了一种具有成本效益的绿色替代品。
• Asymmetric synthesis of spiro 2-pyrrolidin-5-ones, 2-piperidin-6-ones and 1-isoindolin-3-ones. Part 1: N-Acyliminium ion cyclisations with an internal arene nucleophile
  作者：Abood A Bahajaj、Madeleine H Moore、John M Vernon

  DOI：10.1016/j.tet.2003.10.128

  日期：2004.1

  A series of chiral non-racemic 5,5- and 5,6-bicyclic lactams is prepared from (R)-phenylglycinol. These are isomerised on treatment with aluminium trichloride in 1,2-dichloroethane to give spiro lactams in high yield and >3:1 diastereoselectivity. From four structures determined by X-ray crystallography, it follows that spiro indenes are formed preferentially with retention of configuration at the spiro carbon atom and spiro naphthalenes with inversion. (C) 2003 Elsevier Ltd. All rights reserved.