(3S,4S)-4-Amino-6-methyl-hept-1-en-3-ol | 117248-23-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4S)-4-Amino-6-methyl-hept-1-en-3-ol
• 英文别名: (3S,4S)-4-amino-6-methylhept-1-en-3-ol
• CAS: 117248-23-4
• 化学式: C₈H₁₇NO
• 分子量: 143.229
• InChiKey: ZLIBGPHNVLZNQS-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4S)-4-Amino-6-methyl-hept-1-en-3-ol 在 臭氧 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 甲苯 为溶剂， 反应 31.0h， 生成 Benzyl (2E,4R,5S)-7-methyl-4,5-[N-(2,4,6-trimethylphenylsulfonyl)epimino]oct-2-enoate
  参考文献：
  名称：

  Regiospecific ring-opening reactions of β-aziridinyl α,β-enoates with acids: application to the stereoselective synthesis of a couple of diastereoisomeric (E )-alkene dipeptide isosteres from a single β-aziridinyl α,β-enoate and to the convenient preparation of amino alcohols bearing α,β-unsaturated ester groups

  摘要：

  已经发现N-(2,4,6-三甲基苯磺酰)-γ,δ-cis-或-trans-γ,δ-表胺(E)-α,β-烯酸酯与酸如甲磺酸(MSA)或三氟乙酸(TFA)的区域和立体选择性开环反应。这些开环反应对于使用γ,δ-表胺(E)-α,β-烯酸酯单一底物合成一对非对映体(E)-烯二肽同分异构体，以及方便制备δ-氨基γ-羟基α,β-烯酸酯具有重要意义。

  DOI：

  10.1039/a904671b
• 作为产物：
  描述：

  N-叔丁氧羰基-L-亮氨醇 在 氢氧化钾 、 草酰氯 、 sodium hydride 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 (3S,4S)-4-Amino-6-methyl-hept-1-en-3-ol
  参考文献：
  名称：

  A Thermodynamic Preference of Chiral N-Methanesulfonyl and N-Arenesulfonyl 2,3-cis-3-Alkyl-2-Vinylaziridines over Their 2,3-Trans-Isomers:  Useful Palladium(0)-Catalyzed Equilibration Reactions for the Synthesis of (E)-Alkene Dipeptide Isosteres

  摘要：

  Palladium(0)-catalyzed reactions of N-methanesulfonyl- or N-(arenesulfonyl)-3-alkyl-2-vinylaziridines reveal that 2,3-cis-isomers are more stable than the corresponding 2,3-trans-isomers in accord with ab initio calculations. A highly stereoselective synthetic route to (E)-alkene dipeptide isosteres having desired stereochemistries from 2,3-cis-3-isobutyl-2-vinylaziridine by the use of organocopper chemistry is also presented.

  DOI：

  10.1021/jo961760o

文献信息

• Stereoselective vinylation of amino aldehydes using 2-trimethylsilylethylidentriphenylphosphorane
  作者：Maurizio Franciotti、André Mann、Maurizio Taddei

  DOI：10.1016/s0040-4039(00)93602-5

  日期：1991.11

  2-Trimethylsilylethylidentriphenylphosphorane reacts stereoselectively with α-amino aldehydes giving the Cram chelation controlled product of vinylation of the carbonyl group. The olefinic 1,2-amino alcohols obtained with this reaction are important intermediates for the preparation of peptides analogues and they were employed for the preparation of N-Boc-statine.

  2-三甲基甲硅烷基乙基三苯苯基膦烷与α-氨基醛立体选择性地反应，得到羰基乙烯基化的Cram螯合控制产物。通过该反应获得的烯属1,2-氨基醇是制备肽类似物的重要中间体，并且被用于制备N-Boc-他汀。
• A Thermodynamic Preference of Chiral <i>N</i>-Methanesulfonyl and <i>N</i>-Arenesulfonyl 2,3-<i>cis</i>-3-Alkyl-2-Vinylaziridines over Their 2,3-<i>Trans</i>-Isomers:  Useful Palladium(0)-Catalyzed Equilibration Reactions for the Synthesis of (<i>E</i>)-Alkene Dipeptide Isosteres
  作者：Toshiro Ibuka、Norio Mimura、Hiroshi Aoyama、Masako Akaji、Hiroaki Ohno、Yoshihisa Miwa、Tooru Taga、Kazuo Nakai、Hirokazu Tamamura、Nobutaka Fujii、Yoshinori Yamamoto

  DOI：10.1021/jo961760o

  日期：1997.2.1

  Palladium(0)-catalyzed reactions of N-methanesulfonyl- or N-(arenesulfonyl)-3-alkyl-2-vinylaziridines reveal that 2,3-cis-isomers are more stable than the corresponding 2,3-trans-isomers in accord with ab initio calculations. A highly stereoselective synthetic route to (E)-alkene dipeptide isosteres having desired stereochemistries from 2,3-cis-3-isobutyl-2-vinylaziridine by the use of organocopper chemistry is also presented.
• Regiospecific ring-opening reactions of β-aziridinyl α,β-enoates with acids: application to the stereoselective synthesis of a couple of diastereoisomeric (E )-alkene dipeptide isosteres from a single β-aziridinyl α,β-enoate and to the convenient preparation of amino alcohols bearing α,β-unsaturated ester groups
  作者：Hirokazu Tamamura、Masaki Yamashita、Yutaka Nakajima、Kyoko Sakano、Akira Otaka、Hiroaki Ohno、Toshiro Ibuka、Nobutaka Fujii

  DOI：10.1039/a904671b

  日期：——

  Regio- and stereo-selective ring-opening reactions of N-(2,4,6-trimethylphenylsulfonyl)-γ,δ-cis- or -trans-γ,δ-epimino (E)-α,β-enoates with acids such as methanesulfonic acid (MSA) or trifluoroacetic acid (TFA) have been found. These ring-opening reactions are useful for the stereoselective synthesis of a couple of diastereomeric (E)-alkene dipeptide isosteres from a single substrate of γ,δ-epimino (E)-α,β-enoate, and for the convenient preparation of δ-aminated γ-hydroxy α,β-enoates.

  已经发现N-(2,4,6-三甲基苯磺酰)-γ,δ-cis-或-trans-γ,δ-表胺(E)-α,β-烯酸酯与酸如甲磺酸(MSA)或三氟乙酸(TFA)的区域和立体选择性开环反应。这些开环反应对于使用γ,δ-表胺(E)-α,β-烯酸酯单一底物合成一对非对映体(E)-烯二肽同分异构体，以及方便制备δ-氨基γ-羟基α,β-烯酸酯具有重要意义。