3-iodo-4-phenyl-1-oxaspiro[4,5]deca-3,6,9-triene-2,8-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 3-iodo-4-phenyl-1-oxaspiro[4,5]deca-3,6,9-triene-2,8-dione
• 英文别名: 3-iodo-4-phenyl-1-oxaspiro[4.5]deca-3,6,9-trien-2,8-dione；3-Iodo-4-phenyl-1-oxaspiro[4.5]deca-3,6,9-triene-2,8-dione
• 化学式: C₁₅H₉IO₃
• 分子量: 364.139
• InChiKey: ZUBFCPSKZNVSPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-iodo-4-phenyl-1-oxaspiro[4,5]deca-3,6,9-triene-2,8-dione 在 四丁基溴化铵 作用下， 以 乙腈 为溶剂， 生成 3-bromo-4-phenyl-1-oxaspiro[4.5]deca-3,6,9-triene-2,8-dione
  参考文献：
  名称：

  New synthesis of spirocycles by utilizing in situ forming hypervalent iodine species

  摘要：

  使用碘芳烃和 mCPBA 的组合，开发了一种非常有效的螺环化方法，用于安装亲核试剂（Nu = N3、NO2、SCN、SO2Tol 和卤素）经由碘鎓 (III) 盐。以芳基炔烃1和优化的双(碘芳烃)3h为原料，高产率合成了骨架中具有不同官能度的环己二烯酮型螺环化合物2。

  DOI：

  10.1039/c1ob06199b
• 作为产物：
  描述：

  4-methoxyphenyl 3-phenylpropiolate 在 对甲苯磺酸 、 间氯过氧苯甲酸 、 2,2-二碘代联苯 作用下， 以 2,2,2-三氟乙醇 、 水 为溶剂， 反应 3.0h， 生成 3-iodo-4-phenyl-1-oxaspiro[4,5]deca-3,6,9-triene-2,8-dione
  参考文献：
  名称：

  New synthesis of spirocycles by utilizing in situ forming hypervalent iodine species

  摘要：

  使用碘芳烃和 mCPBA 的组合，开发了一种非常有效的螺环化方法，用于安装亲核试剂（Nu = N3、NO2、SCN、SO2Tol 和卤素）经由碘鎓 (III) 盐。以芳基炔烃1和优化的双(碘芳烃)3h为原料，高产率合成了骨架中具有不同官能度的环己二烯酮型螺环化合物2。

  DOI：

  10.1039/c1ob06199b

文献信息

• Discovery and organocatalytic enantioselective construction of axially chiral cyclohexadienylidene skeletons
  作者：Shuai Zhu、Jian-Hui Mao、Jun Kee Cheng、Shao-Hua Xiang、Bin Tan

  DOI：10.1016/j.chempr.2022.06.014

  日期：2022.9

  derived by substituting one C=C double bond of allenes with a cyclohexadienyl moiety. Structurally diverse analogs could be accessed in high efficiency with excellent stereocontrol through two facile and direct synthetic strategies, namely CPA-catalyzed asymmetric dearomatization strategy and enantioselective condensation strategy. Notably, the sterically bulky CPA catalyst plays a central role in the extraordinary

  轴向手性研究已经发展成为现代化学研究的一个组成部分，特别是在不对称催化中。大多数研究都围绕着特殊的轴向手性支架的催化对映选择性构建展开，而替代支架的发现则远远落后。这里描述的是通过用环己二烯基部分取代丙二烯的一个 C=C 双键衍生的轴向手性分子的开发。通过两种简便直接的合成策略，即 CPA 催化的不对称脱芳构化策略和对映选择性缩合策略，可以高效地获得结构多样的类似物，并具有出色的立体控制。值得注意的是，空间庞大的 CPA 催化剂在化学、位点、和脱芳构化策略的对映选择性。这些发现不仅扩展了当前的轴向手性化合物库，而且为探索具有不同骨架的其他轴向手性支架提供了额外的见解。
• Synthesis of Spiro[4.5]trienones by Intramolecular <i>i</i><i>pso</i>-Halocyclization of 4-(<i>p</i>-Methoxyaryl)-1-alkynes
  作者：Xiaoxia Zhang、Richard C. Larock

  DOI：10.1021/ja053079m

  日期：2005.9.1

  A wide variety of 3-halospiro[4.5]trienones are readily prepared in good to excellent yields by the intramolecular ipso-halocyclization of 4-(p-methoxyaryl)-1-alkynes under mild reaction conditions. ICl, I2, and Br2 are all effective electrophiles for this process under carefully optimized reaction conditions.
• Silver-Catalyzed Enantioselective Desymmetrization: Facile Access to Spirolactone-Pyrrolidines Containing a Spiro Quaternary Stereogenic Center
  作者：Kang Liu、Huai-Long Teng、Lu Yao、Hai-Yan Tao、Chun-Jiang Wang

  DOI：10.1021/ol400821q

  日期：2013.5.3

  An unprecedented Ag(I)-catalyzed asymmetric desymmetrization of Spiro cyclohexadienone lactones has been developed successfully, which performs well over a broad scope of substrates and provides a facile access to optically active spirolactone-pyrrolidines in high yields with excellent levels of diastereo-/enantioselectivities.
• Electrophilic <i>ipso</i>-Cyclization of <i>N</i>-(<i>p</i>-Methoxyaryl)propiolamides Involving an Electrophile-Exchange Process
  作者：Bo-Xiao Tang、Qin Yin、Ri-Yuan Tang、Jin-Heng Li

  DOI：10.1021/jo8018297

  日期：2008.11.21

  A novel electrophilic ipso-cyclization involving an electrophile-exchange process has been developed. In the presence of CuX (X = I, Br, SCN) and electrophilic fluoride reagents, a variety of N-(p-methoxyaryl)propiolamides and 4-methoxyphenyl 3-phenylpropiolate were cyclized to selectively afford the corresponding spiro[4.5]decenones in moderate to good yields. It is noteworthy that two azaquaternary tricyclic products were synthesized through a two-step pathway involving an electrophilic ipso-cyclization and then an intramolecular Heck reaction.
• Design, synthesis and anticancer properties of novel oxa/azaspiro[4,5]trienones as potent apoptosis inducers through mitochondrial disruption
  作者：D. Yugandhar、V. Lakshma Nayak、Sivakumar Archana、Kunta Chandra Shekar、Ajay Kumar Srivastava

  DOI：10.1016/j.ejmech.2015.06.050

  日期：2015.8

  A series of twenty seven oxa/azaspiro[4,5]trienone derivatives were synthesized and their anticancer properties have been explored. GI(50) values of all these compounds were evaluated against four types of human cancer cell lines, i.e. MCF-7 (breast), DU-145 (prostate), A549 (lung) and HepG2 (liver). Five compounds of the series exhibited good anticancer potential against MCF-7 with GI(50) values less than 2 mu M. Detailed biological studies of the two representative compounds 9b and 9e revealed that they arrest cell cycle in G0/G1 phase and induce mitochondria mediated apoptosis, that was further confirmed by measurement of mitochondrial membrane potential (Delta Psi m), intracellular ROS generation, caspase 9 activity and Annexin V-FITC assay. Furthermore, western blot analysis suggested that these compounds up-regulate the levels of p53, p21, p27 and Bax, and down-regulate the level of Bcl-2 confirming the apoptosis inducing properties. (C) 2015 Elsevier Masson SAS. All rights reserved.