(S)-3-hydroxy-N,N,4,4-tetramethylpentanamide | 89209-19-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-3-hydroxy-N,N,4,4-tetramethylpentanamide
• 英文别名: (3S)-3-hydroxy-N,N,4,4-tetramethylpentanamide
• CAS: 89209-19-8
• 化学式: C₉H₁₉NO₂
• 分子量: 173.255
• InChiKey: HAUWRDZJRCZVGT-ZETCQYMHSA-N

物化性质

• 沸点：
  266.9±23.0 °C(Predicted)
• 密度：
  0.965±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-hydroxy-4,4-dimethylpentanoic acid 生成 (S)-3-hydroxy-N,N,4,4-tetramethylpentanamide
  参考文献：
  名称：

  Cinquini, Mauro, Phosphorus and Sulfur and the Related Elements, 1985, vol. 24, p. 39 - 72

  摘要：

  DOI：

文献信息

• Asymmetric Hydrogenation of<i>tert</i>-Alkyl Ketones: DMSO Effect in Unification of Stereoisomeric Ruthenium Complexes
  作者：Tomoya Yamamura、Hiroshi Nakatsuka、Shinji Tanaka、Masato Kitamura

  DOI：10.1002/anie.201304408

  日期：2013.8.26

  Face off: The ruthenium complexes of a new axially chiral PNN ligand (L) are highly efficient in the presence of dimethylsulfoxide (DMSO) for hydrogenation of both functionalized and unfunctionalized tert‐alkyl ketones. DMSO is thought to narrow down the many possible complex stereoisomers into a single facial L/Ru complex, thus enhancing the reactivity, selectivity, and productivity.

  面临的挑战：新型的轴向手性PNN配体（L）的钌络合物在二甲基亚砜（DMSO）的存在下对官能化和未官能化叔烷基酮的加氢都非常有效。DMSO被认为可以将许多可能的复杂立体异构体缩小为单个面部L / Ru复杂物，从而提高了反应性，选择性和生产率。
• Asymmetric synthesis of β-hydroxyacetamides mediated by enantiomerically pure sulphinyl derivatives
  作者：Rita Annunziata、Mauro Cinquini、Franco Cozzi、Fernando Montanari、Angelo Restelli

  DOI：10.1016/s0040-4020(01)88812-8

  日期：1984.1

  The aldol-type condensation of enantiomerically pure α-sulphinylacetamides is described. The stereochemical outcome of the reaction mainly depends on the nature of the base used to generate the enolate. Experimental evidences allow the identification of preferred reaction paths.

  描述了对映体纯的α-亚磺酰基乙酰胺的醛醇缩合型。反应的立体化学结果主要取决于用于生成烯醇化物的碱的性质。实验证据可以确定优选的反应路径。
• Direct Catalytic Asymmetric Aldol Reactions of Thioamides: Toward a Stereocontrolled Synthesis of 1,3-Polyols
  作者：Mitsutaka Iwata、Ryo Yazaki、Yuta Suzuki、Naoya Kumagai、Masakatsu Shibasaki

  DOI：10.1021/ja909758e

  日期：2009.12.30

  A direct catalytic asymmetric aldol reaction of thioamides with a soft Lewis acid/hard Brønsted base cooperative catalytic system comprising (R,R)-Ph-BPE/[Cu(CH(3)CN)(4)]PF(6)/LiOAr is described. Highly chemoselective deprotonative activation of thioamides allows for a direct aldol reaction of alpha-nonbranched aliphatic aldehydes, which are susceptible to self-condensation. Facile reduction of the

  硫代酰胺与包含 (R,R)-Ph-BPE/[Cu(CH(3)CN)(4)]PF(6)/LiOAr 的软路易斯酸/硬布朗斯台德碱协同催化体系的直接催化不对称羟醛反应被描述。硫代酰胺的高度化学选择性去质子活化允许 α-非支化脂肪醛的直接羟醛反应，这些醛对自缩合敏感。硫代酰胺官能团的轻松还原和催化剂控制的第二醛醇反应以高度立体选择性的方式提供 1,3-二醇。
• Asymmetric synthesis of β-hydroxythioacetamides mediated by enantiomerically pure sulphiny1 derivatives
  作者：Mauro Cinquini、Amedea Manfredi、Henriette Molinari、Angelo Restelli

  DOI：10.1016/s0040-4020(01)96733-x

  日期：1985.1

  Enantiomerically pure P-tolyl sulphinyl-N,N-dimethylthioacetamide (1) was prepared starting from (-)-(S)-menthyl toluene-p-sulphinate. Aldol-type condensation of (1) and subsequent removal of the Sulphinyl group open an entry to optically active β-hydroxy thioacetamides in 40–90% e.e.

  从（-）-（S）-薄荷基甲苯-对-硫酸酯开始制备对映体纯的对甲苯基亚磺酰基-N，N-二甲基硫代乙酰胺（1）。（1）的醛醇缩合反应和随后的亚磺酰基基团的去除打开了在40-90％ee中进入旋光性β-羟基硫代乙酰胺的通道
• ANNUNZIATA, R.;CINQUINI, M.;COZZI, F.;MONTANARI, F.;RESTELLI, A., TETRAHEDRON, 1984, 40, N 19, 3815-3822
  作者：ANNUNZIATA, R.、CINQUINI, M.、COZZI, F.、MONTANARI, F.、RESTELLI, A.

  DOI：——

  日期：——