nalbuphine | 16676-36-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: nalbuphine
• 英文别名: (4R,4aS,7aR,12bS)-3-(cyclobutylmethyl)-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7,9-triol
• CAS: 16676-36-1
• 化学式: C₂₁H₂₇NO₄
• 分子量: 357.45
• InChiKey: NETZHAKZCGBWSS-QUPQZYKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  73.16
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  在 甲烷磺酸 、 DL-蛋氨酸 作用下， 反应 8.0h， 以47%的产率得到nalbuphine
  参考文献：
  名称：

  O-Demethylation of Opioid Derivatives with Methane Sulfonic Acid/ Methionine: Application to the Synthesis of Naloxone and Analogues

  摘要：

  Naloxone 2 was obtained by demethylation of N-allylnoroxycodone 1 with methane sulfonic acid/methionine. This reagent is an excellent substitute for boron tribromide. It was used for the synthesis of analogous derivatives with variable results.

  DOI：

  10.1080/00397919208019086

文献信息

• Process for the Preparation of Quaternary N-Alkyl Morphinan Alkaloid Salts
  申请人：Wang Peter X.

  公开号：US20100035910A1

  公开（公告）日：2010-02-11

  An improved process for the N-alkylation of tertiary morphinan alkaloid bases to form the corresponding quaternary morphinan alkaloid derivatives.

  将三级吗啡类生物碱进行N-烷基化，形成相应的季铵盐型吗啡类生物碱衍生物的改进过程。
• PROCESS FOR THE PREPARATION OF OPIOID COMPOUNDS
  申请人：NORAMCO, INC.

  公开号：US20150315204A1

  公开（公告）日：2015-11-05

  The present invention is directed to a process for the preparation of opioid compounds such as buprenorphine, naltrexone, naloxone, nalbuphone, nalbuphine, and the like.

  本发明涉及一种制备阿片类化合物（如布洛芬、纳曲酮、纳洛酮、纳布酮、纳布啶等）的方法。
• [EN] PREPARATION OF N-ALKYLATED OPIATES BY REDUCTIVE AMINATION<br/>[FR] PRÉPARATION D'OPIACÉS N-ALKYLÉS PAR AMINATION RÉDUCTRICE
  申请人：MALLINCKRODT INC

  公开号：WO2009012005A1

  公开（公告）日：2009-01-22

  The present invention is directed to the reduction of an N-imine moiety or a hemiaminal moiety of a morphinan in the presence of a ruthenium, rhodium, or iridium asymmetric catalyst and a hydrogen source.

  本发明涉及在存在钌、铑或铱不对称催化剂和氢源的情况下，将吗啉醇类化合物的N-亚胺基团或半胺基团还原的方法。
• PREPARATION OF OPIATE ANALGESICS BY REDUCTIVE ALKYLATION
  申请人：Mitchell Melville

  公开号：US20120046466A9

  公开（公告）日：2012-02-23

  A process for preparing a compound of formula (A), (B) or (C): wherein P is H, CH 3 or a hydroxyl protecting group; X is O, a protected ketone, OH, a protected hydroxyl group or H; Y is OH, a protected hydroxyl group or H; W is C(CH 3 ) 2 OH, C(CH 3 )(C(CH 3 ) 3 )OH or COCH 3 ; Z is C 2 -C 10 alkyl or C 2 -C 10 arylalkyl; and is a single bond or a double bond, is disclosed. The process is a reductive alkylation in the presence of hydrogen and a reductive alkylation catalyst.

  一种制备化合物(A)、(B)或(C)的方法：其中P是H、CH3或羟基保护基；X是O、保护酮、OH、保护羟基或H；Y是OH、保护羟基或H；W是C( )2OH、C( )(C( )3)OH或CO ；Z是C2-C10烷基或C2-C10芳基烷基；并且是单键或双键。该方法是在氢气和还原烷基催化剂的存在下进行还原烷基化反应。
• Preparation of Opiate Analgesics by Reductive Alkylation
  申请人：Mitchell Melville

  公开号：US20080045715A1

  公开（公告）日：2008-02-21

  A process for preparing a compound of formula (A), (B) or (C): wherein P is H, CH 3 or a hydroxyl protecting group; X is O, a protected ketone, OH, a protected hydroxyl group or H; Y is OH, a protected hydroxyl group or H; W is C(CH 3 )OH, C(CH 3 )(C(CH 3 ) 3 )OH or COCH 3 ; Z is C 2 -C 10 alkyl or C 2 -C 10 arylalkyl; and ′ is a single bond or a double bond, is disclosed. The process is a reductive alkylation in the presence of hydrogen and a reductive alkylation catalyst.

  一种制备化合物(A)、(B)或(C)的方法：其中P为H、CH3或羟基保护基；X为O、受保护的酮、OH、受保护的羟基或H；Y为OH、受保护的羟基或H；W为C( )OH、C( )(C( )3)OH或CO ；Z为C2-C10烷基或C2-C10芳基烷基；′为单键或双键。该过程是在氢和还原性烷基化催化剂存在下进行的还原性烷基化反应。