10,11-dihydro-5-hydroxyamino-5H-dibenzo[a,d]cyclopentane

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: 10,11-dihydro-5-hydroxyamino-5H-dibenzo[a,d]cyclopentane
• 英文别名: 2,2'-ethylenediphenylhydroxylamine；dibenzosuber-5-ylhydroxylamine；N-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenyl)hydroxylamine
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: IVMFLJYILJLFGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  10,11-dihydro-5-hydroxyamino-5H-dibenzo[a,d]cyclopentane 在 二异丁基氢化铝 、 sodium fluoride 作用下， 以 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 以69%的产率得到5,6,11,12-Tetrahydro-dibenzazocin
  参考文献：
  名称：

  Regiospecific Rearrangement of Hydroxylamines to Secondary Amines Using Diisobutylaluminum Hydride

  摘要：

  A systematic investigation of a reductive ring-expansion reaction of N-monosubstituted hydroxylamines with diisobutylaluminum hydride (DIBALH) was carried out. The reaction regiospecifically provided a variety of bicyclic or tricyclic heterocycles or linear secondary amines containing nitrogen attached to an aromatic ring.

  DOI：

  10.3987/com-10-s(e)126
• 作为产物：
  描述：

  10,11-二氢二苯并[a,b]环庚烯-5-酮 在 二氯乙酸 、 sodium tetrahydroborate 、 盐酸羟胺 、 sodium acetate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.17h， 生成 10,11-dihydro-5-hydroxyamino-5H-dibenzo[a,d]cyclopentane
  参考文献：
  名称：

  Regiospecific Rearrangement of Hydroxylamines to Secondary Amines Using Diisobutylaluminum Hydride

  摘要：

  A systematic investigation of a reductive ring-expansion reaction of N-monosubstituted hydroxylamines with diisobutylaluminum hydride (DIBALH) was carried out. The reaction regiospecifically provided a variety of bicyclic or tricyclic heterocycles or linear secondary amines containing nitrogen attached to an aromatic ring.

  DOI：

  10.3987/com-10-s(e)126

文献信息

• Gold/Brønsted Acid Relay Catalysis for Enantioselective Construction of Spirocyclic Diketones
  作者：Deyun Qian、Junliang Zhang

  DOI：10.1002/chem.201301208

  日期：2013.5.27

  opportunities: A redox‐, atom‐, and step‐economical asymmetric cascade reaction for the synthesis of chiral spirocyclic architectures with two contiguous stereocenters in high yields and excellent enantioselectivities by using a gold/chiral Brønsted acid relay catalysis system is described (see scheme). The results suggest that the chiral Brønsted acid rather than the chiral gold phosphate complex serves as

  千载难逢的机会：描述了使用金/手性布朗斯台德酸中继催化系统，以高产率和优异对映选择性合成具有两个连续立体中心的手性螺环结构的氧化还原，原子和阶梯经济的不对称级联反应（参见方案） ）。结果表明，手性布朗斯台德酸而不是手性磷酸金配合物是对映体确定步骤的真正催化剂。
• Novel α-Amino Acid-Based Hydroxamic Acid Ligands for Vanadium-Catalyzed Asymmetric Epoxidation of Allylic Alcohols
  作者：Yujiro Hoshino、Hisashi Yamamoto

  DOI：10.1021/ja002602o

  日期：2000.10.1
• Regiospecific Rearrangement of Hydroxylamines to Secondary Amines Using Diisobutylaluminum Hydride
  作者：Hidetsura Cho、Hidetoshi Tokuyama、Kenji Sugimoto、Yusuke Iwama、Nakako Mitsuhashi、Kentaro Okano

  DOI：10.3987/com-10-s(e)126

  日期：——

  A systematic investigation of a reductive ring-expansion reaction of N-monosubstituted hydroxylamines with diisobutylaluminum hydride (DIBALH) was carried out. The reaction regiospecifically provided a variety of bicyclic or tricyclic heterocycles or linear secondary amines containing nitrogen attached to an aromatic ring.