Ditert-butyl 6,7-bis(bromomethyl)-1,4-dihydrophthalazine-2,3-dicarboxylate | 173723-91-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: Ditert-butyl 6,7-bis(bromomethyl)-1,4-dihydrophthalazine-2,3-dicarboxylate
• 英文别名: ditert-butyl 6,7-bis(bromomethyl)-1,4-dihydrophthalazine-2,3-dicarboxylate
• CAS: 173723-91-6
• 化学式: C₂₀H₂₈Br₂N₂O₄
• 分子量: 520.261
• InChiKey: QUVRSUMJPYOAMY-UHFFFAOYSA-N

物化性质

• 沸点：
  514.8±60.0 °C(Predicted)
• 密度：
  1.479±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ditert-butyl 6,7-bis(bromomethyl)-1,4-dihydrophthalazine-2,3-dicarboxylate 在 盐酸 、 4-二甲氨基吡啶 、 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 硝基甲烷 、 氯仿 为溶剂， 反应 14.78h， 生成
  参考文献：
  名称：

  Synthesis and Assembly of New Molecular Hosts:  Solvation and the Energetics of Encapsulation

  摘要：

  Experimental details are given for the preparation of ''softballs'', large self-complementary molecules capable of assembly into pseudo-spherical capsules. Evidence is presented for their existence as hydrogen bonded dimers:in organic solvents, and binding affinities for the reversible encapsulation of smaller molecules of suitable size and shape are given. Studies at various temperatures result in calculated enthalpies and entropies of encapsulation that are positive; accordingly, the process is entropy driven. It is proposed that the hosts in their resting states contain two molecules of solvent such as benzene, and the encapsulation of a single large guest-the hostage-liberates the two solvents. The resulting increase in the number of free molecules gives rise to the increase in entropy observed for the exchange process. Experiments involving solvent mixtures are consistent with this rationale. Calculation of the capsule's interior volume and molecular dynamics simulations support the experimental observations, and hint at unexpected phenomena dealing with the occupancy factors of these systems.

  DOI：

  10.1021/ja962991f
• 作为产物：
  描述：

  二叔丁基叠氮草酸 、 四溴甲苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Ditert-butyl 6,7-bis(bromomethyl)-1,4-dihydrophthalazine-2,3-dicarboxylate
  参考文献：
  名称：

  手性垒球：合成和分子识别特性

  摘要：

  对垒球的不同同源物进行了研究，以探索对映选择性封装的结构变体。尽管单体本身是非手性的，但单体亚基中的两个不同的间隔元件使二聚垒球具有手性。二聚体代表具有不对称腔的胶囊，体积范围为 190 到 390 A(3)。空腔是扭曲的球体，不对称的客体，如天然存在的萜烯，通常更喜欢胶囊的一种对映异构体而不是它的镜像。选择性适中（高达 4:1）。络合研究表明，宿主胶囊足够灵活，可以在客体周围舒适地安排自己，但仍保持足够的刚度，以受到手性客体占用的影响。

  DOI：

  10.1021/ja004080i

文献信息

• Chiral Capsules. 1. Softballs with Asymmetric Surfaces Bind Camphor Derivatives
  作者：Yuji Tokunaga、Julius Rebek

  DOI：10.1021/ja972885t

  日期：1998.1.1

  Self-assembling “softballs” are hollow pseudospherical dimers held together by hydrogen bonds in organic solvents. They encapsulate smaller molecules of suitable size and shape. Stereochemical aspects of these systems are explored through the encapsulation of camphor derivatives. Both symmetrical softballs and those rendered chiral by functional groups on the softball's surface are examined by 1H NMR

  自组装“垒球”是在有机溶剂中通过氢键结合在一起的空心假球形二聚体。它们封装了合适大小和形状的较小分子。这些系统的立体化学方面通过樟脑衍生物的封装进行了探索。对称垒球和由垒球表面的官能团呈现手性的垒球均通过 1 H NMR 方法进行检测。
• Chiral Space in a Unimolecular Capsule
  作者：José M. Rivera、Julius Rebek

  DOI：10.1021/ja0016304

  日期：2000.8.1
• Chiral Softballs:  Synthesis and Molecular Recognition Properties
  作者：José M. Rivera、Tomás Martín、Julius Rebek

  DOI：10.1021/ja004080i

  日期：2001.6.1

  dimeric softball chiral although the monomer itself is achiral. The dimers represent capsules with dissymmetric cavities with volumes ranging from 190 to 390 A(3). The cavities are distorted spheres, and asymmetric guests, such as naturally occurring terpenes, generally prefer one enantiomer of the capsule to its mirror image. The selectivities are moderate (up to 4:1). The complexation studies show that

  对垒球的不同同源物进行了研究，以探索对映选择性封装的结构变体。尽管单体本身是非手性的，但单体亚基中的两个不同的间隔元件使二聚垒球具有手性。二聚体代表具有不对称腔的胶囊，体积范围为 190 到 390 A(3)。空腔是扭曲的球体，不对称的客体，如天然存在的萜烯，通常更喜欢胶囊的一种对映异构体而不是它的镜像。选择性适中（高达 4:1）。络合研究表明，宿主胶囊足够灵活，可以在客体周围舒适地安排自己，但仍保持足够的刚度，以受到手性客体占用的影响。
• Synthesis and Assembly of New Molecular Hosts:  Solvation and the Energetics of Encapsulation
  作者：R. Meissner、X. Garcias、S. Mecozzi、J. Rebek

  DOI：10.1021/ja962991f

  日期：1997.1.1

  Experimental details are given for the preparation of ''softballs'', large self-complementary molecules capable of assembly into pseudo-spherical capsules. Evidence is presented for their existence as hydrogen bonded dimers:in organic solvents, and binding affinities for the reversible encapsulation of smaller molecules of suitable size and shape are given. Studies at various temperatures result in calculated enthalpies and entropies of encapsulation that are positive; accordingly, the process is entropy driven. It is proposed that the hosts in their resting states contain two molecules of solvent such as benzene, and the encapsulation of a single large guest-the hostage-liberates the two solvents. The resulting increase in the number of free molecules gives rise to the increase in entropy observed for the exchange process. Experiments involving solvent mixtures are consistent with this rationale. Calculation of the capsule's interior volume and molecular dynamics simulations support the experimental observations, and hint at unexpected phenomena dealing with the occupancy factors of these systems.