N-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)-4-methylbenzenesulfonamide | 141666-88-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)-4-methylbenzenesulfonamide
• 英文别名: N-[[(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methyl]-4-methylbenzenesulfonamide
• CAS: 141666-88-8
• 化学式: C₂₇H₃₇NO₂S
• 分子量: 439.662
• InChiKey: DIKWDPZDTRXYBO-GMQQYTKMSA-N

物化性质

• 沸点：
  550.8±60.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)-4-methylbenzenesulfonamide 在 sodium hydride 、 N-氟代双苯磺酰胺 作用下， 以 二氯甲烷 、 mineral oil 为溶剂， 生成 N-fluoro-N-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  铜催化、N 定向的远端 C(sp3)–H 功能化对 Azepanes

  摘要：

  我们在此报道了铜催化的N-氟磺酰胺和 1,3-二烯/1,3-烯炔的正式 [5 + 2] 氮杂环化反应，用于合成结构多样的含烯烃/炔烃的氮杂环庚烷。该反应具有选择性功能化远端未活化的 C(sp 3 )–H 键和广泛的底物范围，从而允许对药物和天然产物进行后期修饰。提出了一种涉及 N-自由基的 1,5-氢原子转移、烷基自由基与 1,3-二烯/1,3-烯炔的轻松偶联以及通过 C-N 键形成构建氮杂环庚烷基序的自由基机制。

  DOI：

  10.1021/acs.orglett.2c03135
• 作为产物：
  描述：

  氢化松香 、 对甲苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  手性高价碘催化实现了不寻常的区域分散分子间烯烃氨氧化反应

  摘要：

  本文描述了一种新型碘化物催化分子间氨氧化策略。酰胺用作 O 源和 N 源来探测区域控制策略。值得注意的是，可以选择性地引入简单的添加剂，以实现电子活化烯烃的区域发散的氧胺化过程，同时对未活化的烯烃进行区域互补。我们的初步数据表明，这种基于亲核试剂的区域控制策略也可以应用于使用手性高价碘催化的不对称过程。

  DOI：

  10.1021/jacsau.1c00103

文献信息

• Correction to “A Radical Smiles Rearrangement Promoted by Neutral Eosin Y as a Direct Hydrogen Atom Transfer Photocatalyst”
  作者：Jianming Yan、Han Wen Cheo、Wei Kiat Teo、Xiangcheng Shi、Hui Wu、Shabana Binte Idres、Lih-Wen Deng、Jie Wu

  DOI：10.1021/jacs.2c10485

  日期：2022.11.23

  Page 11360. In Table 3 of our Communication, we inadvertently drew the incorrect structures for epiandrosterone (stereoisomer was drawn instead), (+)-fenchol (incorrect position of the methyl group), and (+)-dehydroabietylamine (incorrect position of quaternary carbon center with methylamine and methyl substituents), which are incorporated in our products 6a, 6c, and 6f, respectively. Reactions were

  第 11360 页。在我们通讯的表 3 中，我们无意中绘制了表雄酮的错误结构（改为绘制了立体异构体）、(+)-苯酚（甲基的错误位置）和 (+)-脱氢松香胺（季铵盐的错误位置）具有甲胺和甲基取代基的碳中心），它们分别包含在我们的产品6a、6c和6f中。反应在表 1 中的标准条件下进行。获得了两种异构体的混合物，并显示了总体分离产量。未绘制的异构体表示 (4 S ,5 S) 在异噻唑烷二酮部分的构型。两种异构体的其他手性中心构型相同。通过手性 HPLC 分析估计两种异构体的比例。两种异构体的比例通过分析粗1 H NMR 光谱确定。这些绘图错误已在此处显示的表 3 中得到更正。作为进一步的说明，在第 11358 页的最后一段中，首先讨论了表 3，句子“此外，由 (+)-脱氢枞胺、d-丙氨酸和d-苯丙氨酸制备的N-芳基磺酰基丙醇酰胺也提供了相应的产品6d–6f顺利”应更正为“此外，N由d-苯丙氨酸、d-丙氨酸和
• Reductive deprotection of allyl, benzyl and sulfonyl substituted alcohols, amines and amides using a naphthalene-catalysed lithiation
  作者：Emma Alonso、Diego J. Ramón、Miguel Yus

  DOI：10.1016/s0040-4020(97)00920-4

  日期：1997.10

  The reaction of different protected alcohols, amines and amides with lithium and a catalytic amount of naphthalene (4 mol %) in THF at low temperature leads to their deprotection under very mild reaction conditions, the process being in many cases chemoselective. (C) 1997 Elsevier Science Ltd.
• (+)-Dehydroabietylamine derivatives target triple-negative breast cancer
  作者：Taotao Ling、My Tran、Miguel A. González、Lekh Nath Gautam、Michele Connelly、Rachael K. Wood、Iram Fatima、Gustavo Miranda-Carboni、Fatima Rivas

  DOI：10.1016/j.ejmech.2015.07.034

  日期：2015.9

  Breast cancer remains the leading cause of cancer-related death among women. The invasive triple-negative subtype is unresponsive to estrogen therapy, and few effective treatments are available. In search of new chemical scaffolds to target this disease, we conducted a phenotypic screen against the human breast carcinoma cell lines MDA-MB-231, MA11, and MCF-7 using terrestrial natural products. Natural products that preferentially inhibited proliferation of triple-negative MDA-MB-231 cells over estrogen receptor positive cells were further studied; herein we focused on the abietanes. The activity of the abietane carnosol prompted us to generate a focus library from the readily available (+)-dehydroabietylamine. The lead compound 61 displayed a promising EC50 of 9.0 mu M against MDA-MB-231 and our mechanistic studies indicate it induced apoptosis, which was associated with activation of caspase-9 and -3 and the cleavage of PARP. Here we describe our current progress towards this promising therapeutic candidate. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Visible-Light-Promoted Remote C(sp³)–H Amidation and Chlorination
  作者：Qixue Qin、Shouyun Yu

  DOI：10.1021/acs.orglett.5b00582

  日期：2015.4.17

  A visible-light-promoted C(sp(3))-H amidation and chlorination of N-chlorosulfonamides (NCSs) is reported. This remote C(sp(3))-H functionalization can be achieved in weak basic solution at room temperature with as little as 0.1 mol % of a photocatalyst. A variety of nitrogen-containing heterocycles (up to 94% yield) and chlorides (up to 93% yield) are prepared from NCSs. Late-stage C(sp3)H functionalization of complex and biologically important (-)-cis-myrtanylamine and (+)-dehydroabietylamine derivatives can also be achieved with excellent yields and regioselectivity.
• Convenient halodeamination and hydrodeamination of primary amines.
  作者：Frank S. Guziec、Dongchu Wei

  DOI：10.1021/jo00040a010

  日期：1992.7

  Treatment of p-toluenesulfonamides of primary amines with 2 equiv of chloroamine at room temperature in the presence of base leads to reductive deamination. If excess chloroamine is present, the corresponding alkyl or aryl halides are obtained instead in good yields. Both reactions presumably proceed via tosylhydrazine and diazene intermediates; the course of the reaction is often governed by steric hindrance. Treatment of the isolated tosylhydrazine intermediate with base and chloroamine, bromine, or iodine also leads to the corresponding halides in very good yields.