4-phenylbutylhydroxylamine | 851228-77-8

• 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: 4-phenylbutylhydroxylamine
• 英文别名: Benzenebutanamine, N-hydroxy-；N-(4-phenylbutyl)hydroxylamine
• CAS: 851228-77-8
• 化学式: C₁₀H₁₅NO
• 分子量: 165.235
• InChiKey: XUTPBEFGJJKJNC-UHFFFAOYSA-N

物化性质

• 沸点：
  310.2±35.0 °C(Predicted)
• 密度：
  1.022±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-phenylbutylhydroxylamine 在 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 3-((R)-2-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl)-5-methyl-2-(4-phenyl-butyl)-isoxazolidine-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Practical Synthesis and Evaluation of the Biological Activities of 1α,25-dihydroxyvitamin D₃ Antagonists, 1α,25-dihydroxyvitamin D₃-26,23-lactams. Designed on the Basis of the Helix 12-Folding Inhibition Hypothesis

  摘要：

  A practical synthetic route to novel vitamin D antagonists of DLAM (1 alpha.,25-dihydroxyvitamin D-3-26,23lactam) was developed from vitamin D-2 via the 1,3-dipolar cycloaddition reaction as a key step. Six DLAM derivatives (24 compounds) with a variety of nitrogen substituents and stereochemistries at C23 and C25 were synthesized. Among these new derivatives, (23S,25S)-DLAM isomers bound effectively to VDRs and showed antagonistic activity in the HL-60 cell differentiation inhibition assay. The importance of the substituent on the nitrogen of DLAMs for antagonistic activity was also suggested by computational docking studies.

  DOI：

  10.1021/jm050738x
• 作为产物：
  描述：

  4-苯基丁醛 在 吡啶 、 盐酸 、 甲醇 、 盐酸羟胺 、 sodium cyanoborohydride 作用下， 以 水 为溶剂， 反应 18.25h， 生成 4-phenylbutylhydroxylamine
  参考文献：
  名称：

  酰胺自由基的净 1,2-氢原子转移：用于合成 1,2-二胺衍生物

  摘要：

  氢原子转移 (HAT) 过程是选择性构建 C(sp 3 )–C(sp 3 ) 键的最有用的方法之一。具有以杂原子为中心的基团（O • 、N • ）的1,5-HAT 已得到广泛应用，并且相对于其他1, n -HAT 工艺更受青睐。相比之下，净 1,2-HAT 过程很少被观察到。在此，报道了第一个酰胺基自由基比 1,5-HAT 优先经历净 1,2-HAT。从 2-氮杂烯丙基阴离子到N-烷基N-芳氧基酰胺的单电子转移开始，后者产生酰胺基。酰胺基自由基经过 net-1,2-HAT 生成以 C 为中心的自由基，该自由基参与与 2-氮杂烯丙基自由基的分子间自由基-自由基偶联，生成 1,2-二胺衍生物。机理和 EPR 实验指向自由基中间体。密度泛函理论计算为碱辅助、逐步 1,2-HAT 过程提供支持。有人提出，在碱性条件下酰胺基自由基的生成可以大大扩展，以得到α-氨基C-中心自由基，这将作为有价值的合成中间体。

  DOI：

  10.1021/jacs.3c04376

文献信息

• Amidyl Radical Directed Remote Allylation of Unactivated sp ³ C−H Bonds by Organic Photoredox Catalysis
  作者：Kui Wu、Lushun Wang、Sonivette Colón‐Rodríguez、Gerd‐Uwe Flechsig、Ting Wang

  DOI：10.1002/anie.201811004

  日期：2019.2.4

  visible‐light‐mediated allylation of unactivated sp3 C−H bonds is reported. The remote allylation was directed by the amidyl radical, which was generated by photocatalytic fragmentation of a pre‐functionalized amide precursor. Both aromatic and aliphatic amide derivatives could successfully deliver the remote C−H allylation products in good yields. A variety of electron deficient allyl sulfone systems could

  报道了未激活的sp 3 C-H键的可见光介导的烯丙基化的发展。远程烯丙基化是由酰胺基进行的，该酰胺基是由预官能化酰胺前体的光催化裂解生成的。芳香族和脂肪族酰胺衍生物均可成功地以高收率交付偏远的CH烯丙基化产物。多种缺电子的烯丙基砜系统可用作δ-碳自由基受体。
• Vitamin D3 lactam derivative
  申请人：Nagasawa Kazuo

  公开号：US20050182032A1

  公开（公告）日：2005-08-18

  Compounds expressed by the following formula (1) or pharmaceutically permissible solvate thereof which is effective for treating Paget's disease of bone, hypercalcemia or osteoporosis. In the formula, R 1 is a C 2 -C 10 alkyl group, or a C 7 -Cl 5 aralkyl group whose aromatic ring is optionally substituted with a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxyl group, a hydroxyl group, a halogen atom or a trifluoromethyl group; and R 2 is a C 1 -C 10 alkyl group, or a C 7 -C 15 aralkyl group whose aromatic ring is optionally substituted with a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxyl group, a hydroxyl group, a halogen atom or a trifluoromethyl group.

  由以下公式（1）表示的化合物或其药学上可接受的溶剂化合物，对治疗骨骼帕吉特病、高钙血症或骨质疏松症有效。在该公式中，R1是C2-C10烷基基团，或者是一个C7-C15芳基烷基基团，其芳香环可选择地被C1-C6烷基基团、C1-C6甲氧基基团、羟基、卤原子或三氟甲基取代；而R2是一个C1-C10烷基基团，或者是一个C7-C15芳基烷基基团，其芳香环可选择地被C1-C6烷基基团、C1-C6甲氧基基团、羟基、卤原子或三氟甲基取代。
• [EN] UREA-CONTAINING HYDROXYETHYLAMINE COMPOUNDS AS RETROVIRAL PROTEASE INHIBITORS<br/>[FR] COMPOSES D'HYDROXYETHYLAMINE CONTENANT DE L'UREE UTILISES COMME INHIBITEURS DE PROTEASES RETROVIRALES
  申请人：G.D. SEARLE & CO.

  公开号：WO1993023368A1

  公开（公告）日：1993-11-25

  (EN) Compounds represented by formula (I) or a pharmaceutically acceptable salt, prodrug or ester thereof, wherein A represents radicals represented by formulae (A1, A2, A3) (values for the variables given herein), are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.(FR) L'invention concerne des composés représentés par la formule (I) ou un sel, un promédicament ou un ester pharmaceutiquement acceptable de ceux-ci, formule dans laquelle A représente des radicaux représentés par les formules (A1, A2, A3) (valeurs pour les variables ci-incluses). Lesdits composés constituent d'efficaces inhibiteurs de protéases rétrovirales, et notamment de protéase du VIH.

  化合物的化学式为(I)，或其药学上可接受的盐、前药或酯，其中A代表由公式(A1、A2、A3)表示的基团（变量的值在此给出），它们是有效的逆转录病毒蛋白酶抑制剂，特别是HIV蛋白酶的抑制剂。
• VITAMIN D3 LACTAM DERIVATIVE
  申请人：Teijin Pharma Limited

  公开号：EP1683786A1

  公开（公告）日：2006-07-26

  A Compound represented by the following formula (1) or pharmaceutically acceptable solvate thereof which is useful for treating Paget's disease of bone, hypercalcemia or osteoporosis. In the formula, R1 is a C2-C10 alkyl group, or a C7-C15 aralkyl group whose aromatic ring is optionally substituted with a C1-C6 alkyl group, a C1-C6 alkoxy group, a hydroxy group, a halogen atom or a trifluoromethyl group; and R2 is a C1-C10 alkyl group, or a C7-C15 aralkyl group whose aromatic ring is optionally substituted with a C1-C6 alkyl group, a C1-C6 alkoxy group, a hydroxy group, a halogen atom or a trifluoromethyl group.

  一种由下式（1）代表的化合物或其药学上可接受的溶液，可用于治疗骨的 Paget 病、高钙血症或骨质疏松症。 式中，R1 是 C2-C10 烷基或 C7-C15 芳基，其芳香环任选被 C1-C6 烷基、C1-C6 烷氧基、羟基、卤素原子或三氟甲基取代；R2 是 C1-C10 烷基或 C7-C15 芳基，其芳香环任选被 C1-C6 烷基、C1-C6 烷氧基、羟基、卤素原子或三氟甲基取代。
• Synthesis and evaluation of N-(phenylalkyl)acetohydroxamic acids as potential substrates for N-arylhydroxamic acid N,O-acyltransferase
  作者：Adnan A. Elfarra、Heui Mei Yeh、Patrick E. Hanna

  DOI：10.1021/jm00352a018

  日期：1982.10

  N-(4-Phenylcyclohexyl)acetohydroxamic acid and a series of N-(phenylalkyl)acetohydroxamic acids were synthesized and evaluated as substrates for partially purified rat and hamster hepatic arylhydroxamic acid N,O-acyltransferase systems (AHAT). The compounds were assayed for their abilities to function as acetyl donors in the AHAT-mediated transacetylation of 4-aminoazobenzene and for their abilities to participate in the AHAT-mediated conversion of N-arylhydroxylamines to electrophilic intermediates that form methylthio adducts upon reaction with N-acetylmethionine. None of the newly synthesized compounds displayed significant activity in either of the assays. The results of this study indicate that acetohydroxamic acids that have the nitrogen atom of the hydroxamic acid group attached directly to aliphatic or cycloalkyl groups are not likely to serve as substrates or inhibitors of AHAT.