2-(S)-aminooctadecan-3-one hydrochloride | 378755-81-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(S)-aminooctadecan-3-one hydrochloride
• 英文别名: (2S)-2-Amino-3-octadecanone hydrochloride；(2S)-2-aminooctadecan-3-one;hydrochloride
• CAS: 378755-81-8
• 化学式: C₁₈H₃₇NO*ClH
• 分子量: 319.959
• InChiKey: CJIILUGXXXKRTA-LMOVPXPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  43.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-tert-butyl-N-(3-oxooctadecan-2-yl)carbamate 在 乙酰氯 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以110 mg的产率得到2-(S)-aminooctadecan-3-one hydrochloride
  参考文献：
  名称：

  一些非典型鞘氨醇碱基的合成与表征

  摘要：

  鞘脂是所有真核生物和某些原核生物中普遍存在的丰富组成部分。鞘脂不仅在不同物种之间而且在单个细胞内都显示出很大的结构多样性。该品种不仅限于例如鞘糖脂的极性头基的改变，而且一方面影响由不同脂肪酸组成的亲脂性锚，另一方面影响由不同鞘氨醇碱基组成的亲脂性锚。例如在病原体中的不同鞘氨醇碱基内的结构变异可用于鉴定新的生物标志物和药物靶标，并且常见和不常见鞘脂的概况的特定变化与诸如糖尿病或癌症的病理状况相关。所以，鞘脂血症的新兴领域致力于收集细胞鞘脂组的数据，从而将其中的变化分配给细胞的某些状态或病理状况。但是，这种强大的工具仍然受到有关单个脂质种类的结构信息的可用性以及适用于定量的内部标准的限制。在本文中，我们描述了各种1-脱氧-鞘氨醇碱的合成。1-脱氧鞘脂由于其在罕见的遗传性神经病HSAN1中的病理作用，而且还作为II型糖尿病的预测性生物标志物，最近获得了广泛的关注。已经使用了本文合成和表征的某些化

  DOI：

  10.1016/j.bmc.2018.06.031

文献信息

• Antitumoral compounds
  申请人：——

  公开号：US20040048834A1

  公开（公告）日：2004-03-11

  New spisulosine derivatives of use in treating tumors are of the formula (I) wherein: each X is the same or different, and represents H, OH, OR′, SH, SR′, SOR′, SO 2 R′, NO 2 , NH 2 , NHR′, N(R′) 2 , CN, halogen, C(═O)H, C(═O)CH 3 , CO 2 H, CO 2 CH 3 , substituted or unsubstituted C 1 -C 18 alkyl, substituted or unsubstituted C 2 -C 18 alkenyl, substituted or unsubstituted C 2 -C 18 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaromatic, or two groups X may together form ═O; Y is NR 1 , OR 1 , PR 1 , SR 1 , or halogen, wherein the number of substituents R 1 is selected to suit the valency and each R 1 is independently selected of H, OH, C(═O)R′, P(═O)R′R″, substituted or unsubstituted C 1 -C 18 alkyl, substituted or unsubstituted C 2 -C 18 alkenyl, substituted or unsubstituted C 2 -C 18 alkynyl, substituted or unsubstituted aryl, and wherein the dotted line indicates an optional double bond; each Z is the same different, and represents H, OH, OR′, SH, SR′, SOR′, SO 2 R′, NO 2 , NH 2 , NHR′, N(R′) 2 , NHC(O)R′, CN, halogen, C(═O)H, C(═O)CH 3 , CO 2 H, CO 2 CH 3 , substituted or unsubstituted C 1 -C 18 alkyl, substituted or unsubstituted C 2 -C 18 alkenyl, substituted or unsubstituted C 2 -C 18 alkenyl, substituted or unsubstituted C 2 -C 18 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaromatic, or two groups Z may together form ═O; z is 0 to 25; y is to 0 to 20; R 2 is H, C(═O)R′, P(═O)R′R″, S(═O)R′R″, S(═O) 2 R′, substituted or unsubstituted C 1 -C 18 alkyl, substituted or unsubstituted C 2 -C 18 Alkenyl, substituted or unsubstituted C 2 -C 18 alkynyl, substituted or unsubstituted aryl; R 3 is H, C(═O)R′, P(═O)R′R″, S(═O)R′R″, S(═O) 2 R′, substituted or unsubstituted C 1 -C 18 alklyl, substituted or unsubstituted C 2 -C 18 alkenyl, substituted or unsubstituted C 2 -C 18 alkynyl, substituted or unsubstituted aryl; each of the R′, R″ groups is independently selected from the group consisting of H, OH, NO 2 , NH 2 , SH, CN, halogen, ═O, C(═O)H, C(═O)CH 3 , CO 2 H, CO 2 CH 3 , substituted or unsubstituted C 1 -C 18 alkyl, substituted or unsubstituted C 1 -C 18 alkoxy, substituted or unsubstituted C 2 -C 18 alkenyl, substituted or unsubstituted C 2 -C 18 alkynl, substituted or unsubstituted aryl; there may be one or more unsaturations in the hydrocarbon backbone defined by the chain (II) and salts thereof; with the exception of a C 16 -C 24 2-amino-3-hydroxyalkane or a C 16 -C 24 2-amino-3-hydroxyalkene.

  新的用于治疗肿瘤的斯皮苏林衍生物的化学式为（I），其中：每个X相同或不同，表示H、OH、OR′、SH、SR′、SOR′、SO2R′、NO2、NH2、NHR′、N(R′)2、CN、卤素、C(═O)H、C(═O)CH3、CO2H、CO2CH3、取代或未取代的C1-C18烷基、取代或未取代的C2-C18烯基、取代或未取代的C2-C18炔基、取代或未取代的芳基、取代或未取代的杂芳基，或两个X基团可能共同形成═O；Y为NR1、OR1、PR1、SR1或卤素，其中取代基R1的数量选择以适应化合价，每个R1独立选择自H、OH、C(═O)R′、P(═O)R′R″、取代或未取代的C1-C18烷基、取代或未取代的C2-C18烯基、取代或未取代的C2-C18炔基、取代或未取代的芳基，虚线表示可选的双键；每个Z相同或不同，表示H、OH、OR′、SH、SR′、SOR′、SO2R′、NO2、NH2、NHR′、N(R′)2、NHC(O)R′、CN、卤素、C(═O)H、C(═O)CH3、CO2H、CO2CH3、取代或未取代的C1-C18烷基、取代或未取代的C2-C18烯基、取代或未取代的C2-C18炔基、取代或未取代的芳基、取代或未取代的杂芳基，或两个Z基团可能共同形成═O；z为0至25；y为0至20；R2为H、C(═O)R′、P(═O)R′R″、S(═O)R′R″、S(═O)2R′、取代或未取代的C1-C18烷基、取代或未取代的C2-C18烯基、取代或未取代的C2-C18炔基、取代或未取代的芳基；R3为H、C(═O)R′、P(═O)R′R″、S(═O)R′R″、S(═O)2R′、取代或未取代的C1-C18烷基、取代或未取代的C2-C18烯基、取代或未取代的C2-C18炔基、取代或未取代的芳基；每个R′、R″基团独立选择自H、OH、NO2、NH2、SH、CN、卤素、═O、C(═O)H、C(═O)CH3、CO2H、CO2CH3、取代或未取代的C1-C18烷基、取代或未取代的C1-C18烷氧基、取代或未取代的C2-C18烯基、取代或未取代的C2-C18炔基、取代或未取代的芳基；碳链（II）中的碳氢骨架中可能存在一个或多个不饱和度，及其盐；除了C16-C242-氨基-3-羟基烷或C16-C242-氨基-3-羟基烯。
• ANTITUMORAL COMPOUNDS
  申请人：PHARMA MAR, S.A.

  公开号：EP1287006A1

  公开（公告）日：2003-03-05
• US7138547B2
  申请人：——

  公开号：US7138547B2

  公开（公告）日：2006-11-21
• [EN] ANTITUMORAL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSES ANTITUMORAUX
  申请人：PHARMA MAR SA

  公开号：WO2001094357A1

  公开（公告）日：2001-12-13

  New spisulosine derivatives of use in treating tumors are of the formula (I) wherein: each X is the same or different, and represents H, OH, OR', SH, SR', SOR', SO2R', NO2, NH2, NHR', N(R')2, CN, halogen, C(=O)H, C(=O)CH3, CO2H, CO2CH3, substituted or unsubstituted C1-C18 alkyl, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C18 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaromatic, or two groups X may together form =O; Y is NR1, OR1, PR1, SR1, or halogen, wherein the number of substituents R1 is selected to suit the valency and each R1 is independently selected of H, OH, C(=O)R', P(=O)R'R'', substituted or unsubstituted C1-C18 alkyl, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C18 alkynyl, substituted or unsubstituted aryl, and wherein the dotted line indicates an optional double bond; each Z is the same different, and represents H, OH, OR', SH, SR', SOR', SO2R', NO2, NH2, NHR', N(R')2, NHC(O)R', CN, halogen, C(=O)H, C(=O)CH3, CO2H, CO2CH3, substituted or unsubstituted C1-C18 alkyl, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C18 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaromatic, or two groups Z may together form =O; z is 0 to 25; y is to 0 to 20; R2 is H, C(=O)R', P(=O)R'R'', S(=O)R'R'', S(=O)2R', substituted or unsubstituted C1-C18 alkyl, substituted or unsubstituted C2-C18 Alkenyl, substituted or unsubstituted C2-C18 alkynyl, substituted or unsubstituted aryl; R3 is H, C(=O)R', P(=O)R'R'', S(=O)R'R'', S(=O)2R', substituted or unsubstituted C1-C18 alkyl, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C18 alkynyl, substituted or unsubstituted aryl; each of the R', R'' groups is independently selected from the group consisting of H, OH, NO2, NH2, SH, CN, halogen, =O, C(=O)H, C(=O)CH3, CO2H, CO2¿CH¿3, substituted or unsubstituted C1-C18 alkyl, substituted or unsubstituted C1-C18 alkoxy, substituted or unsubstituted C2-C18 alkenyl, substituted or unsubstituted C2-C18 alkynyl, substituted or unsubstituted aryl; there may be one or more unsaturations in the hydrocarbon backbone defined by the chain (II) and salts thereof; with the exception of a C16-C24 2-amino-3-hydroxyalkane or a C16-C24 2-amino-3-hydroxyalkene.
• Synthesis and characterization of some atypical sphingoid bases
  作者：Essa M. Saied、Thuy Linh-Stella Le、T. Hornemann、Christoph Arenz

  DOI：10.1016/j.bmc.2018.06.031

  日期：2018.8

  of appropriate internal standards for quantification. Herein we describe the synthesis of a variety of 1-deoxy-sphingoid bases. 1-DeoxySphingolipids have recently acquired significant attention due to its pathological role in the rare inherited neuropathy, HSAN1 but also as predictive biomarkers in diabetes type II. Some of the compounds synthesized and characterized herein, have been used and will

  鞘脂是所有真核生物和某些原核生物中普遍存在的丰富组成部分。鞘脂不仅在不同物种之间而且在单个细胞内都显示出很大的结构多样性。该品种不仅限于例如鞘糖脂的极性头基的改变，而且一方面影响由不同脂肪酸组成的亲脂性锚，另一方面影响由不同鞘氨醇碱基组成的亲脂性锚。例如在病原体中的不同鞘氨醇碱基内的结构变异可用于鉴定新的生物标志物和药物靶标，并且常见和不常见鞘脂的概况的特定变化与诸如糖尿病或癌症的病理状况相关。所以，鞘脂血症的新兴领域致力于收集细胞鞘脂组的数据，从而将其中的变化分配给细胞的某些状态或病理状况。但是，这种强大的工具仍然受到有关单个脂质种类的结构信息的可用性以及适用于定量的内部标准的限制。在本文中，我们描述了各种1-脱氧-鞘氨醇碱的合成。1-脱氧鞘脂由于其在罕见的遗传性神经病HSAN1中的病理作用，而且还作为II型糖尿病的预测性生物标志物，最近获得了广泛的关注。已经使用了本文合成和表征的某些化