(S)-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester | 212557-00-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester
• 英文别名: (S)-1-benzyloxycarbonyl-2-(hydroxymethyl)piperidine；(S)-1-benzyloxycarbonyl-2-hydroxymethylpiperidine；benzyl (2S)-2-(hydroxymethyl)piperidine-1-carboxylate；(S)-Benzyl 2-(hydroxymethyl)piperidine-1-carboxylate
• CAS: 212557-00-1
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: UDGDHNGWPNSYCD-ZDUSSCGKSA-N

物化性质

• 沸点：
  396.4±25.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester 在 palladium on activated charcoal 正丁基锂 、 草酰氯 、 氢气 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 为溶剂， -70.0~25.0 ℃ 、310.27 kPa 条件下， 反应 8.0h， 生成 (R)-2-丙基哌啶
  参考文献：
  名称：

  Short syntheses of (S)-pipecolic acid, (R)-coniine, and (S)-δ-coniceine using biocatalytically-generated chiral building blocks

  摘要：

  The kinetic resolutions of both (+/-)-N-(benzyloxycarbonyl-2-(hydroxymethyl)piperidine [(+/-)-5] and (+/-)-N(tert-butoxycarbonyi)-2-(hydroxymethyl)piperidine [(+/-)-6] catalyzed by the enzyme acylase I from Aspergillus species (AA-I) afforded the chiral building blocks (S)-5 and (S)-6, respectively; which were used for the syntheses of the title natural products and derivatives of (S)-pipecolic acid. The syntheses were short (2-4 steps) and proceeded with satisfactory overall yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00178-5
• 作为产物：
  描述：

  (S)-N-cbz-哌啶-2-甲醛 在 sodium tetrahydroborate 作用下， 生成 (S)-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Construction of Chiral 2-Functionalized PiperidineviaEnzymatic Resolution and Palladium-catalyzed N-Alkylation

  摘要：

  通过酶解外消旋醇 (1) 得到的光学活性脲[(-)-1]在钯催化下发生环化反应，生成了哌啶 6。该反应实现了高效的分子内手性转移。化合物 6 被转化为 (+)- 科尼因和 2- 羟甲基哌啶。

  DOI：

  10.1246/cl.1994.21

文献信息

• [EN] SORDARIN DERIVATIVES FOR PREVENTING OR TREATING INFECTIOUS DISEASES CAUSED BY PATHOGENIC MICROORGANISMS<br/>[FR] DÉRIVÉS DE SORDARINE POUR PRÉVENIR OU TRAITER DES MALADIES INFECTIEUSES CAUSÉES PAR DES MICRO-ORGANISMES PATHOGÈNES
  申请人：ASTELLAS PHARMA INC

  公开号：WO2009131246A1

  公开（公告）日：2009-10-29

  This invention relates to a new sordarin derivative or a pharmaceutically acceptable salt thereof, which has antimicrobial activities (especially, antifungal activities), to process for preparation thereof, to a pharmaceutical composition comprising the same, and to a method for prophylactic and/or therapeutic treatment of infectious diseases in a human being or an animal.

  这项发明涉及一种新的索达林衍生物或其药用可接受的盐，该衍生物具有抗菌活性（特别是抗真菌活性），其制备方法，包含该衍生物的药物组合物，以及用于预防或治疗人类或动物传染性疾病的方法。
• A concise diastereoselective approach to (+)-dexoxadrol, (−)-epi-dexoxadrol, (−)-conhydrine and (+)-lentiginosine from (−)-pipecolinic acid
  作者：Chinmay Bhat、Santosh G. Tilve

  DOI：10.1016/j.tet.2013.10.082

  日期：2013.12

  A new diastereoselective pathway for the total synthesis of (+)-dexoxadrol, first asymmetric synthesis of (−)-epi-dexoxadrol and formal synthesis of conhydrine and (+)-lentiginosine is presented using commercially available (−)-pipecolinic acid. The key reactions utilized are Sharpless asymmetric dihydroxylation and Wittig reaction. The paper further describes the study of effect of protecting groups

  使用市售的（-）-哌啉酸，提出了一种新的非对映选择性途径，用于全合成（+）-右氧杂醇，（-）-表-右氧杂戊醇的首次不对称合成以及Conhydroine和（+）-lentiginosine的形式合成。使用的关键反应是Sharpless不对称二羟基化反应和Wittig反应。该论文进一步描述了保护基对哌啶环系统中末端烯烃的二羟基化作用的研究。
• Stereoselective synthesis of (+)- and (−)-lentiginosine
  作者：Mk Gurjar、Lakshmi Ghosh、M Syamala、V Jayasree

  DOI：10.1016/s0040-4039(00)78520-0

  日期：1994.11

  Simple routes to (1,2,8a)- and (1,2,8a)-lentiginosine have been described, based on Sharpless asymmetric dihydroxylation, starting from ()- and ()-pipecolinic acids.

  简单路由到（1 ，2 ，图8a ） -和（1 ，2 ，8α ）-lentiginosine已经描述的基础上，Sharpless不对称二羟基化，从（起始） -和（）-pipecolinic酸。
• Henry–Nef reaction: a practical and versatile chiral pool route to 2-substituted pyrrolidine and piperidine alkaloids
  作者：Chinmay Bhat、Santosh G. Tilve

  DOI：10.1016/j.tet.2013.05.055

  日期：2013.7

  for the synthesis of 2-substituted pyrrolidine and piperidine alkaloids containing 1,3-aminoketone and 1,3-amino alcohol units. The utility of the protocol is demonstrated by asymmetric synthesis of 12 natural products of which asymmetric synthesis of (−)-N-methylpelletierine is presented for the first time. The one-carbon homologation described also provides an alternate route for the synthesis of key

  本文描述了由亨利和Nef组合反应开发的协同方案，用于合成含有1,3-氨基酮和1,3-氨基醇单元的2-取代的吡咯烷和哌啶生物碱。该协议的实用性通过12种天然产物的不对称合成得到了证明，其中首次出现了（-）- N-甲基胆碱的不对称合成。所描述的一碳同系物还提供了另一种合成关键中间体高脯氨醇和高胡椒醇的中间体的途径，这些中间体用作几种生物碱的合成前体，并由α-氨基酸构建β-氨基酸。
• [EN] PDD AND BPD COMPOUNDS<br/>[FR] COMPOSÉS DDP ET BPD
  申请人：FEMTOGENIX LTD

  公开号：WO2016198869A1

  公开（公告）日：2016-12-15

  The invention relates to pyrridinobenzodiazepines (PDDs) comprising three fused 6-7- 6–membered rings and to benzopyrridodiazecines (BPDs) comprising three fused 6-8- 6–membered rings and, in particular, to PDD or BPD dimers linked together or PDD and BPD monomers linked to aromatic groups, and pharmaceutically acceptable salts thereof, which are useful as medicaments, such as anti-proliferative agents. PDDs and BPDs may be represented by formula (I): and salts or solvates thereof, wherein R2, R4-R6 and R8 are independently selected substituent groups; and either: (i) R9 and R10 together form a double bond; (ii) R9 is H and R10 is OH; or (iii) R9 is H and R10 is ORA and RA is C1-6 alkyl; wherein each of m, n, u and w may be 0 or 1; where (a) the compound is a dimer with each monomer being the same or different and being of formula (I) where one of R1, R2, R3 and R7 of the first monomer and one of R'1, R'2, R3 and R'7 of the second monomer form together a bridge having the formula –X-L-X'- linking the monomers and m + n + u + w = 1; or (b) a dimer and one of R1, R2 and R3 of the first monomer and one of R'1, R'2 and R3 of the second monomer form together a bridge having the formula –X-L-X'- linking the monomers and m = n = u = w = o; or (c) one of R1, R2, R3 and R7 has the formula: –X- L-X'-D or -(CH2)f-O-R14 and m + n + u + w = o or 1; or (d) R7 has the formula: –X-L-X'- D or -(CH2)g-O -15 and m + n + u + w = 1; and X-L-X'- is a linker group and D has the formula (II) or (III):

  该发明涉及到包含三个融合的6-7-6环的吡啶苯二氮杂环己烷（PDDs）以及包含三个融合的6-8-6环的苯基吡啶二氮杂环己烷（BPDs），特别是涉及到连接在一起的PDD或BPD二聚体或连接到芳香基团的PDD和BPD单体，以及其药用可接受盐，这些化合物可用作药物，如抗增殖剂。PDDs和BPDs可以用以下公式（I）表示：以及其盐或溶剂化合物，其中R2、R4-R6和R8是独立选择的取代基团；并且：（i）R9和R10共同形成双键；（ii）R9为H且R10为OH；或（iii）R9为H且R10为ORA，RA为C1-6烷基；其中m、n、u和w中的每个可能为0或1；其中（a）该化合物是一个二聚体，每个单体相同或不同且为公式（I）的其中一个，其中第一个单体的R1、R2、R3和R7中的一个和第二个单体的R'1、R'2、R3和R'7中的一个共同形成具有公式-X-L-X'-的桥连接单体，且m + n + u + w = 1；或（b）一个二聚体，第一个单体的R1、R2和R3中的一个和第二个单体的R'1、R'2和R3中的一个共同形成具有公式-X-L-X'-的桥连接单体，且m = n = u = w = o；或（c）R1、R2、R3和R7中的一个具有以下公式：-X-L-X'-D或-(CH2)f-O-R14，且m + n + u + w = o或1；或（d）R7具有以下公式：-X-L-X'-D或-(CH2)g-O-15，且m + n + u + w = 1；而X-L-X'-是一个连接基团，D具有以下公式（II）或（III）。