(S)-1-isopropylallylamine hydrochloride

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-1-isopropylallylamine hydrochloride
• 英文别名: valine-derived allylic amine hydrochloride salt；[(3S)-4-methylpent-1-en-3-yl]azanium;chloride
• 化学式: C₆H₁₃N*ClH
• 分子量: 135.637
• InChiKey: YWYUQZZRADDIQG-FYZOBXCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.56
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  27.6
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-1-isopropylallylamine hydrochloride 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (5S)-2-(tert-butyldimethylsilyl)oxy-5-N-(1-(S)-isopropylallyl)phenyl-2-(phenylseleno)acetyl-1,3-oxazolidin-4-one
  参考文献：
  名称：

  Oxyoxazolidinone as an auxiliary for heterocyclic synthesis. Enantioselective formation of N-unprotected 2-pyrrolidones from selenocarboxylate and allylamines via radical cyclization

  摘要：

  Optic ally active N-unprotected 2-pyrrolidones were prepared in a highly stereoselective manner through radical cyclization reaction of oxyoxazolidinone. Asymmetric induction from the oxyoxazolidinone ring system was generally high and oxazabicyclo[3.3.0]-octanones were obtained in good yields. Treatment of the bicyclic compounds with TBAF resulted in the one-step cleavage of C-O and C-N bond. directly giving secondary 2-pyrrolidones in good yields along with recovery of chiral mandelic acid without loss of optical purity. The use of the present procedure gave optically active 4,5-disubstituted N-unprotected 2-pyrrolidone derivatives trans selectively. (C) 2003 Elsevier Ltd. All fights reserved.

  DOI：

  10.1016/s0040-4020(03)01015-9
• 作为产物：
  描述：

  乙烯基溴化镁 、 (R,E)-2-methyl-N-(2-methylpropylidene)propane-2-sulfinamide 在 盐酸 作用下， 以 乙醚 、 二氯甲烷 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 0.5h， 生成 (S)-1-isopropylallylamine hydrochloride 、 (R)-4-methylpent-1-en-3-amine hydrochloride
  参考文献：
  名称：

  通过有机金属试剂的高度非对映1,2-增补不对称合成手性胺的ñ -叔-butanesulfinyl亚胺

  摘要：

  对于有机金属试剂的1,2-增补高产量和高立体选择性的方法ñ -叔-butanesulfinyl醛亚胺（2）和Ñ -叔-butanesulfinyl酮亚胺（3）中描述。已证明将烷基，芳基，烯基和烯丙基碳负离子添加到具有不同空间和电子特性的各种亚胺中。亚磺酰胺产物（4和6）的酸性甲醇分解可提供高度对映体富集的α-支化和α，α-二支化胺。由于很容易从醛和酮中获得广泛的亚磺酰基亚胺，因此可以制备多种对映体富集的胺。

  DOI：

  10.1016/s0040-4020(99)00451-2

文献信息

• Ring-Closing Metathesis Strategies to Cyclic Sulfamide Peptidomimetics
  作者：Joseph M Dougherty、Donald A Probst、Randall E Robinson、Joel D Moore、Thomas A Klein、Kelley A Snelgrove、Paul R Hanson

  DOI：10.1016/s0040-4020(00)00885-1

  日期：2000.12

  sulfamides and sulfonyl carbamates to generate both symmetric and unsymmetric cyclic sulfamides. Two strategies are revealed, one centers on the RCM reaction of allylated sulfamides 9a–e to generate the C2-symmetric cyclic sulfamides 4a–e in high yields. A second RCM strategy utilizes the known sulfonyl carbamate 15 to prepare unsymmetric cyclic sulfamides 16 and 6 in two four-step sequences. Overall

  讨论了合成许多受约束的磺酰胺的闭环复分解（RCM）策略。该方法利用了磺酰胺和磺酰基氨基甲酸酯的内在化学性质来生成对称和不对称的环状磺酰胺。揭示了两种策略，一种集中在烯丙基化磺酰胺9a - e的RCM反应上，以高产率生成C 2-对称环状磺酰胺4a - e。第二种RCM策略是利用已知的氨基磺酸磺酰基酯15制备不对称的环状磺酰胺16和6分两个四个步骤。总体而言，所描述的路线适用于代表新的拟肽支架的多种受约束的二肽磺酰胺的合成。
• Amino acid-derived, 7-membered cyclic sulfamides and methods of synthesizing the same
  申请人：University of Kansas

  公开号：US06359129B1

  公开（公告）日：2002-03-19

  New sulfamide compounds and methods of forming those compounds are provided. The inventive methods comprise subjecting a template opened-ring sulfamide compound to a ring-closing metathesis reaction in the presence of a Grubbs catalyst to yield a heterocyclic sulfamide. Advantageously, the template structures can be provided with a wide array of functional groups (e.g., substituted and unsubstituted amino acid side chains, peptides) chosen to provide particular properties to the compound. The preferred heterocyclic sulfamides are represented by a formula selected from the group consisting of

  提供了新的磺胺化合物和形成这些化合物的方法。创新的方法包括将一个模板开环磺胺化合物置于格氏催化剂存在下进行环闭合芳构反应，以产生一个杂环磺胺化合物。优点是，模板结构可以配有各种功能基团（例如，取代和未取代的氨基酸侧链、肽），以赋予化合物特定的性质。优选的杂环磺胺化合物由以下组成的公式代表：
• New strategies to symmetric and unsymmetric cyclic sulfamide analogs of DMP 323: a ‘sulfur linchpin’/RCM approach
  作者：Jung Ho Jun、Joseph M Dougherty、Marı́a del Sol Jiménez、Paul R Hanson

  DOI：10.1016/j.tet.2003.04.001

  日期：2003.11

  The synthesis of 7-membered cyclic sulfamides utilizing the RCM reaction is described herein. Two major synthetic strategies that expand the scope and utility of our previously reported sulfamide and sulfamoyl carbamate chemistry are employed. Both Mitsunobu alkylation and simple alkylation of core sulfamides and sulfamoyl carbamates coupled with RCM are used to efficiently install lipophilic groups

  本文描述了利用RCM反应的7元环硫酰胺的合成。使用了两种主要的合成策略，这些策略扩大了我们先前报道的氨磺酰胺和氨基磺酸氨基磺酰基化学反应的范围和实用性。Mitsunobu烷基化以及核心磺酰胺和氨基甲酸酯氨基甲酸酯与RCM的简单烷基化都可用于将亲脂性基团有效地安装到环状磺酰胺的P1 / P1'和P2 / P2'外围。总体而言，所描述的路线适用于各种环状7元磺酰胺的合成。
• A Temporary Phosphorus Tether/Ring-Closing Metathesis Strategy to Functionalized 1,4-Diamines
  作者：Kevin T. Sprott、Matthew D. McReynolds、Paul R. Hanson

  DOI：10.1021/ol016828n

  日期：2001.11.1

  [GRAPHICS]The synthesis of 1,4-diamines containing the (Z)-1,4-diaminobut-2-ene subunit via a temporary phosphorus tether/RCM strategy is described. We have developed a new method utilizing phosphorus nuclei as suitable temporary tethers for the coupling of nonracemic allylic amines. This approach allows for the generation of C-2-symmetric and unsymmetric 1,4-diamines 1-3, which may have considerable synthetic and biological utility. This represents the first synthetic pathway for the expedient coupling of two amines via a temporary tether approach.
• Sprott; McReynolds; Hanson, Synthesis, 2001, # 4, p. 612 - 620
  作者：Sprott、McReynolds、Hanson

  DOI：——

  日期：——