(S)-N⁴,N⁵-di-i-butoxycarbonyl-4,5-diaminopentyl methanesulfonate | 1542135-34-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (S)-N⁴,N⁵-di-i-butoxycarbonyl-4,5-diaminopentyl methanesulfonate
• 英文别名: (S)-4,5-bis((isobutoxycarbonyl)amino)pentyl methanesulfonate；[(4S)-4,5-bis(2-methylpropoxycarbonylamino)pentyl] methanesulfonate
• CAS: 1542135-34-1
• 化学式: C₁₆H₃₂N₂O₇S
• 分子量: 396.505
• InChiKey: LDWDEWWTJBBYOA-AWEZNQCLSA-N

物化性质

• 沸点：
  574.4±45.0 °C(predicted)
• 密度：
  1.146±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-N⁴,N⁵-di-i-butoxycarbonyl-4,5-diaminopentyl methanesulfonate 、 二甲胺 以 四氢呋喃 为溶剂， 反应 15.0h， 以88%的产率得到(S)-N¹,N²-di-i-butoxycarbonyl-N⁵,N⁵-dimethyl-1,2,5-triaminopentane
  参考文献：
  名称：

  [EN] TRANSITION METAL COMPLEXES FOR ENANTIOSELECTIVE CATALYSIS OF CARBON-CARBON, CARBON-HETEROATOM, AND CARBON-HYDROGEN BOND FORMING REACTIONS
  [FR] COMPLEXES DE MÉTAL DE TRANSITION POUR LA CATALYSE ÉNANTIOSÉLECTIVE DE RÉACTIONS DE FORMATION DE LIAISONS CARBONE-CARBONE, CARBONE-HÉTÉROATOME ET CARBONE-HYDROGÈNE

  摘要：

  公开号：

  WO2014018978A3
• 作为产物：
  描述：

  (S)-(+)-5-羟甲基-2-吡咯烷酮对甲苯磺酸酯 在 N-甲基吗啉 、 盐酸 、 sodium azide 、 palladium on activated charcoal 、 氢气 、 三乙胺 、 potassium hydroxide 、 氯甲酸异丁酯 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 (S)-N⁴,N⁵-di-i-butoxycarbonyl-4,5-diaminopentyl methanesulfonate
  参考文献：
  名称：

  Synthesis of a series of ω-dimethylaminoalkyl substituted ethylenediamine ligands for use in enantioselective catalysis

  摘要：

  The title compounds H2NCH((CH2)(n)NMe2)CH2NH2 L1-1A (n = 1-4) are efficiently synthesized in enantiopure form. The commercial starting materials, L-asparagine, (S)-5-hydroxymethy1-2-pyrrolidinone, and (S)-6-(((benzyloxy)carbonyI)-amino)-2-((tert-butoxycarbonyl)amino)hexanoic acid, are elaborated in 6-9 standard steps to giye Ll (18% overall), 12 (13%), L3 (36%) and LA (38%) or the corresponding tris(hydrochloric acid) salts [H3NCH((CH2)(n)NHMe2)CH2NH3](3+) 3Cl(-), which are preferable for long term storage. The sequences make use of isobutyl carbamate, Cbz, and Boc protecting groups and Hofmann type rearrangements; the dimethylamino groups are introduced at late stages, either via reductive dimethylations or nucleophilic displacements involving mesylates and HNMe2. L1-L4 chelate to [Co(en)(2)](3+) fragments to give octahedral complexes that catalyze numerous enantioselective reactions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.09.012

文献信息

• TRANSITION METAL COMPLEXES FOR ENANTIOSELECTIVE CATALYSIS OF CARBON-CARBON, CARBON-HETEROATOM, AND CARBON-HYDROGEN BOND FORMING REACTIONS
  申请人：THE TEXAS A&M UNIVERSITY SYSTEM

  公开号：US20150165429A1

  公开（公告）日：2015-06-18

  In some embodiments, the present disclosure pertains to a compound, comprising a transition metal complex having the formula Φ-[M(x,y)-L 1 (w,v)-L 2 (t,u)-L 3 ] p+ An − m Z − p — m . In an embodiment of the present disclosure Φ may be A. In another embodiment Φ may be Δ. In some embodiments of the present disclosure, M is a transition metal. In a related embodiment, p is an integer corresponding to the oxidation state of M. In some embodiments of the present disclosure, each of x, y, w, v, t, and u independently comprise R. In other embodiments, each of x, y, w, v, t, and u independently comprise S. In an embodiment of the present disclosure, each of L 1 , L 2 , and L 3 independently is a ligand comprising a substituted diamine. In some embodiments, An″ comprises a lipophilic anion, where m is from 1 to 3, and where Z − comprises an optional second anion.

  在某些实施例中，本公开涉及一种化合物，包括具有公式Φ-[M（x，y）-L1（w，v）-L2（t，u）-L3]p+An−mZ−p—m的过渡金属配合物。在本公开的某种实施例中，Φ可以是A。在另一种实施例中，Φ可以是Δ。在本公开的某些实施例中，M是一种过渡金属。在相关实施例中，p是与M的氧化态相对应的整数。在本公开的某些实施例中，x，y，w，v，t和u中的每个都独立地包括R。在其他实施例中，x，y，w，v，t和u中的每个都独立地包括S。在本公开的某种实施例中，L1、L2和L3中的每个都独立地是包含取代二胺的配体。在某些实施例中，An″包括一个亲脂性阴离子，其中m从1到3，而Z−包括一个可选的第二个阴离子。
• Transition metal complexes for enantioselective catalysis of carbon-carbon, carbon-heteroatom, and carbon-hydrogen bond forming reactions
  申请人：The Texas A&M University System

  公开号：US09446393B2

  公开（公告）日：2016-09-20

  In some embodiments, the present disclosure pertains to a compound, comprising a transition metal complex having the formula Φ-[M(x,y)-L1(w,v)-L2(t,u)-L3]p+An−mZ−p_m. In an embodiment of the present disclosure Φ may be A. In another embodiment Φ may be Δ. In some embodiments of the present disclosure, M is a transition metal. In a related embodiment, p is an integer corresponding to the oxidation state of M. In some embodiments of the present disclosure, each of x, y, w, v, t, and u independently comprise R. In other embodiments, each of x, y, w, v, t, and u independently comprise S. In an embodiment of the present disclosure, each of L1, L2, and L3 independently is a ligand comprising a substituted diamine. In some embodiments, An″ comprises a lipophilic anion, where m is from 1 to 3, and where Z− comprises an optional second anion.

  在某些实施例中，本公开涉及一种化合物，包括具有以下公式的过渡金属配合物Φ-[M（x，y）-L1（w，v）-L2（t，u）-L3]p+An−mZ−p_m。在本公开的一种实施例中，Φ可以是A。在另一种实施例中，Φ可以是Δ。在本公开的某些实施例中，M是过渡金属。在相关实施例中，p是与M的氧化态相对应的整数。在本公开的某些实施例中，x、y、w、v、t和u中的每个独立地包括R。在其他实施例中，x、y、w、v、t和u中的每个独立地包括S。在本公开的一种实施例中，L1、L2和L3中的每个独立地是包含取代二胺的配体。在某些实施例中，An″包括一个亲脂性阴离子，其中m为1到3，Z−包括一个可选的第二阴离子。
• [EN] TRANSITION METAL COMPLEXES FOR ENANTIOSELECTIVE CATALYSIS OF CARBON-CARBON, CARBON-HETEROATOM, AND CARBON-HYDROGEN BOND FORMING REACTIONS<br/>[FR] COMPLEXES DE MÉTAL DE TRANSITION POUR LA CATALYSE ÉNANTIOSÉLECTIVE DE RÉACTIONS DE FORMATION DE LIAISONS CARBONE-CARBONE, CARBONE-HÉTÉROATOME ET CARBONE-HYDROGÈNE
  申请人：TEXAS A & M UNIV SYS

  公开号：WO2014018978A3

  公开（公告）日：2014-04-10
• US9446393B2
  申请人：——

  公开号：US9446393B2

  公开（公告）日：2016-09-20
• Synthesis of a series of ω-dimethylaminoalkyl substituted ethylenediamine ligands for use in enantioselective catalysis
  作者：Subrata K. Ghosh、Carola Ganzmann、John A. Gladysz

  DOI：10.1016/j.tetasy.2015.09.012

  日期：2015.12

  The title compounds H2NCH((CH2)(n)NMe2)CH2NH2 L1-1A (n = 1-4) are efficiently synthesized in enantiopure form. The commercial starting materials, L-asparagine, (S)-5-hydroxymethy1-2-pyrrolidinone, and (S)-6-(((benzyloxy)carbonyI)-amino)-2-((tert-butoxycarbonyl)amino)hexanoic acid, are elaborated in 6-9 standard steps to giye Ll (18% overall), 12 (13%), L3 (36%) and LA (38%) or the corresponding tris(hydrochloric acid) salts [H3NCH((CH2)(n)NHMe2)CH2NH3](3+) 3Cl(-), which are preferable for long term storage. The sequences make use of isobutyl carbamate, Cbz, and Boc protecting groups and Hofmann type rearrangements; the dimethylamino groups are introduced at late stages, either via reductive dimethylations or nucleophilic displacements involving mesylates and HNMe2. L1-L4 chelate to [Co(en)(2)](3+) fragments to give octahedral complexes that catalyze numerous enantioselective reactions. (C) 2015 Elsevier Ltd. All rights reserved.