(R,R)-2-chloro-N-[2-(chloroacetylamino)cyclohexyl]acetamide | 53719-89-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R,R)-2-chloro-N-[2-(chloroacetylamino)cyclohexyl]acetamide
• 英文别名: (R,R)-2-chloro-N-[2-(2-chloro-acetylamino)cyclohexyl]acetamide；N,N'-bis(chloroacetyl)-trans-1,2-diaminocyclohexane；2-chloro-N-[(1R,2R)-2-[(2-chloroacetyl)amino]cyclohexyl]acetamide
• CAS: 53719-89-4
• 化学式: C₁₀H₁₆Cl₂N₂O₂
• 分子量: 267.155
• InChiKey: NXWRKAARNQHEEG-HTQZYQBOSA-N

物化性质

• 沸点：
  523.4±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R,R)-2-chloro-N-[2-(chloroacetylamino)cyclohexyl]acetamide 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 乙二醇二甲醚 、 N,N-二甲基乙酰胺 为溶剂， 反应 33.5h， 生成 2R,3R,8R,9R-bis(cyclohexano)-1,4,7,10,13-pentaazacyclopentadecane
  参考文献：
  名称：

  Toward the Rational Design of Superoxide Dismutase Mimics:  Mechanistic Studies for the Elucidation of Substituent Effects on the Catalytic Activity of Macrocyclic Manganese(II) Complexes

  摘要：

  Two new isomeric bis(trans-fused cyclohexano) substituted 1,4,7,10,13-pentaazacyclopentadecane ligands and their Mn(II) complexes, 3 and 14, have been synthesized, and their activity as superoxide dismutase (SOD) catalysts has been studied. Complex 3 is an excellent SOD catalyst with a second-order rate constant at pH 7.4 of 1.2 x 10(+8) M-1 s(-1). In contrast, the isomeric complex 4 has virtually no detectable catalytic SOD activity, implying the need to understand the effect that the position, number, and stereochemistry of substituents exert on the catalytic rate. The crystal structure of the complex 4 was determined and reveals that the Mn(II) ion is coordinated in a pentagonal bipyramid array of the dye nitrogens of the macrocyclic ligand and capped by two trans-chloro ligands. Crystal data for MnC18H37Cl2N5 are as follows: triclinic at 20 degrees C, space group P-1-C(i)2 (no. 2); a = 9.746(3) Angstrom, b = 12.631(6) Angstrom, c = 11.311(5) Angstrom; alpha = 73.14(4)degrees, beta = 76.39(3)degrees, gamma = 79.98(3)degrees, V = 1287(1) Angstrom(3), and Z = 2 (rho(calc) = 1.279 g/cm(3); mu(2) Mo K-alpha = 6.23 mm(-1)). Mechanistic studies with the complex 3 and the pentamethyl susbstituted complex, 5, including D2O rate studies, are reported and are consistent with the existence of two pathways for the rate-determining electron-transfer from Mn(II) to superoxide: (1) hydrogen atom transfer from a bound water on Mn(IP) to HO2. to yield a Mn(III) hydroxo intermediate and (2) the dissociative pathway in which superoxide anion binds to a vacant coordination site on Mn(II) followed by protonation/oxidation to yield a Mn(III)hydroperoxo species. Subsequent reduction of the intermediate Mn(III) with superoxide anion completes the catalytic cycle. Substituent effects on the rates and relative contribution of the two pathways to the overall rate of SOD activity is ascribed to the propensity of the ligand to fold around Mn(II) forming a pseudo-octahedral complex similar in geometry to the oxidized Mn(III) complex. Folding of the pentaaza macrocyclic ligand is confirmed as a relevant structural motif for this series of Mn(TI) complexes by the X-ray structure determination of the bis(nitrate) derivative of 1, [Mn(C10H25N5)NO3]NO3, which reveals a six-coordinate structure with a folded conformation of the macrocyclic ligand. Crystal data for [Mn(C10H25N5)NO3]NO3: orthorhombic at -100 degrees C, space group P2(1)2(1)2(1); a = 9.457(2) Angstrom, b = 12.758(2) Angstrom, c = 13.834(2) Angstrom, V = 1669.1(5) Angstrom(3), and Z = 4 (rho(calc) = 1.549 g/cm(3)).

  DOI：

  10.1021/ja964271e
• 作为产物：
  描述：

  氯乙酰氯 、 (1R,2R)-(+)-1,2-环己二胺 L-酒石酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 以95%的产率得到(R,R)-2-chloro-N-[2-(chloroacetylamino)cyclohexyl]acetamide
  参考文献：
  名称：

  A practical and efficient synthesis of chiral N,N-disubstituted C2 symmetric diamines derived from (R,R)-1,2-diaminocyclohexane

  摘要：

  An improved synthesis of chiral diamine ligands derived from (R,R)-1,2-diaminocyclohexane is described, providing N-substituted diamines. The synthesis of other neu ligands based on this methodology, is also reported. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00198-7

文献信息

• Thiols and Selenols as Electron-Relay Catalysts for Disulfide-Bond Reduction
  作者：John C. Lukesh、Brett VanVeller、Ronald T. Raines

  DOI：10.1002/anie.201307481

  日期：2013.12.2

  Pass them on! Dithiobutylamine immobilized on a resin is a useful reagent for the reduction of disulfide bonds. Its ability to reduce a disulfide bond in a protein is enhanced greatly if used along with a soluble strained cyclic disulfide or mixed diselenide that relays electrons from the resin to the protein. This electron‐relay catalysis system provides distinct advantages over the use of excess

  传给他们！固定在树脂上的二硫代丁胺是还原二硫键的有用试剂。如果与将电子从树脂传递到蛋白质的可溶性应变环状二硫键或混合二硒化物一起使用，它减少蛋白质中二硫键的能力会大大增强。与单独使用过量的可溶性还原剂相比，这种电子中继催化系统具有明显的优势。
• New conformationally constrained polyaza macrocycles prepared via the bis(chloroacetamide) method
  作者：Patrick J. Lennon、Hayat Rahman、Karl W. Aston、Susan L. Henke、Dennis P. Riley

  DOI：10.1016/s0040-4039(00)75981-8

  日期：1994.1

  The synthesis of two new series of conformationally constrained polyazamacrocycles featuring polysubstitution at macrocycle ring carbons is described.

  描述了两个新的一系列构象受限的聚氮杂大环化合物的合成，其特征是在大环环碳上具有多取代基。
• Methods of preparing manganese complexes of nitrogen-containing
  申请人：Monsanto Company

  公开号：US05610293A1

  公开（公告）日：1997-03-11

  The present invention is directed to low molecular weight mimics of superoxide dismutase (SOD) represented by the formula: ##STR1## wherein R, R', R.sub.1, R'.sub.1, R.sub.2, R'.sub.2, R.sub.3, R'.sub.3, R.sub.4, R'.sub.4, R.sub.5, R'.sub.5, R.sub.6, R'.sub.6, R.sub.7, R'.sub.7, R.sub.8, R'.sub.8, R.sub.9, and R'.sub.9 and X, Y, Z and n are as defined herein, useful as therapeutic agents for inflammatory disease states and disorders, ischemic/reperfusion injury, stroke, atherosclerosis, hypertension and all other conditions of oxidant-induced tissue damage or injury.

  本发明涉及超氧化物歧化酶（SOD）的低分子量模拟物，其表示为以下式子：##STR1## 其中R，R'，R1，R'1，R2，R'2，R3，R'3，R4，R'4，R5，R'5，R6，R'6，R7，R'7，R8，R'8，R9和R'9以及X，Y，Z和n如本文所定义，可用作治疗炎症性疾病状态和障碍，缺血/再灌注损伤，中风，动脉硬化，高血压以及所有其他氧化剂引起的组织损伤或损伤的治疗剂。
• Manganese complexes of nitrogen-containing macrocyclic ligands effective
  申请人：——

  公开号：US05637578A1

  公开（公告）日：1997-06-10

  The present invention is directed to low molecular weight mimics of superoxide dismutase (SOD) represented by the formula: ##STR1## wherein R, R', R.sub.1, R'.sub.1, R.sub.2, R'.sub.2, R.sub.3, R'.sub.3, R.sub.4, R'.sub.4, R.sub.5, R'.sub.5, R.sub.6, R'.sub.6, R.sub.7, R'.sub.7, R.sub.8, R'.sub.8, R.sub.9, and R'.sub.9 and X, Y, Z and n are as defined herein, useful as therapeutic agents for inflammatory disease states and disorders, ischemic/reperfusion injury, stroke, atherosclerosis, hypertension and all other conditions of oxidant-induced tissue damage or injury.

  本发明涉及超氧化物歧化酶（SOD）的低分子量模拟物，其化学式为：##STR1## 其中R、R'、R1、R'1、R2、R'2、R3、R'3、R4、R'4、R5、R'5、R6、R'6、R7、R'7、R8、R'8、R9和R'9以及X、Y、Z和n的定义如本文所述，作为治疗炎症性疾病状态和紊乱、缺血/再灌注损伤、中风、动脉粥样硬化、高血压以及其他氧化剂引起的组织损伤或损伤的治疗剂使用。
• Hepatobiliary tetraazamacrocyclic magnetic resonance contrast agents
  申请人：Bristol-Myers Squibb

  公开号：US05358704A1

  公开（公告）日：1994-10-25

  Novel compounds of the formula ##STR1## and metal chelates of the compounds are useful particularly for MRI of the hepatobiliary system.

  公式为##STR1##的新化合物以及这些化合物的金属螯合物，特别适用于肝胆系统的MRI。