tert-butyl N-[2-(3-methoxybut-1-ynyl)phenyl]carbamate | 1262034-09-2

• 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: tert-butyl N-[2-(3-methoxybut-1-ynyl)phenyl]carbamate
• CAS: 1262034-09-2
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: AXNLZCZLPMTREW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[2-(3-methoxybut-1-ynyl)phenyl]carbamate 在 4-二甲氨基吡啶 、 sodium carbonate 、 potassium carbonate 、 platinum(II) chloride 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 15.67h， 生成 Tert-butyl 3-formyl-2-[1-[1-[(2-methylpropan-2-yl)oxycarbonyl]indol-3-yl]ethyl]indole-1-carboxylate
  参考文献：
  名称：

  WO2019200232A5

  摘要：

  公开号：

  WO2019200232A5
• 作为产物：
  描述：

  2-碘苯胺 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 4.84h， 生成 tert-butyl N-[2-(3-methoxybut-1-ynyl)phenyl]carbamate
  参考文献：
  名称：

  MALASSEZIN AND ANALOGS THEREOF AS SKIN BRIGHTENING AGENTS

  摘要：

  本发明涉及用于美白皮肤的化合物、组合物和方法。本发明的化合物、组合物和方法通常涉及由Malassezia酵母产生的化合物及其化学类似物。除了用于美白皮肤的应用外，本发明的化合物、组合物和方法还可用于调节黑色素细胞活性、诱导黑色素细胞凋亡、激活芳烃受体（AhR）、改善由于色素沉着紊乱引起的色素沉着过度，并调节黑色素生成、黑色素体生物合成和黑色素体转移。

  公开号：

  US20170260133A1

文献信息

• SYNTHESIS OF DIINDOLYLMETHANES AND INDOLO[3,2-B]CARBAZOLES, COMPOUNDS FORMED THEREBY, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20160039754A1

  公开（公告）日：2016-02-11

  Described is a method to make diindolylmethanes and indolyl/pyrrolylmethanes, The method includes the steps of contacting an ether comprising an arylpropargyl moiety and an amine-protected, substituted or unsubstituted aniline moiety with a substituted or unsubstituted indol or a substituted or unsubstituted pyrrole, in the presence of a metal-containing catalyst, for a time and at a temperature to cause an annulation/arylation cascade reaction that yields a diindolylmethane or a indolyl/pyrrolylmethane. The resulting compounds are effective to modulate activity of arylhydrocarbon receptors, to inhibit activity of PCSK9, and to stimulate secretion of glucagon-like peptide 1 in mammals.

  描述了一种制备二吲哚基甲烷和吲哚基/吡咯基甲烷的方法。该方法包括以下步骤：在金属催化剂的存在下，使包含芳基炔丙基部分和胺保护的、取代的或未取代的苯胺部分的醚与取代的或未取代的吲哚或取代的或未取代的吡咯接触，接触一段时间和温度，以引发环化/芳基化级联反应，从而产生二吲哚基甲烷或吲哚基/吡咯基甲烷。所得化合物能有效调节芳基烃受体的活性，抑制PCSK9的活性，并刺激哺乳动物胰高血糖素样肽1的分泌。
• Platinum(II)-Catalyzed Generation and [3+2] Cycloaddition Reaction of α,β-Unsaturated Carbene Complex Intermediates for the Preparation of Polycyclic Compounds
  作者：Kodai Saito、Hideyuki Sogou、Takuya Suga、Hiroyuki Kusama、Nobuharu Iwasawa

  DOI：10.1021/ja108586d

  日期：2011.2.2

  Pt(II)-catalyzed generation of unsaturated carbene complex intermediates from various propargyl ether derivatives based on electrophilic activation of alkynes was realized. These in situ generated unsaturated carbene complexes undergo [3+2] cycloaddition reaction with various vinyl ethers, leading to efficient formation of indoles, naphthols, and benzofuran fused with a five-membered ring in high yields

  基于炔烃的亲电活化，实现了 Pt(II) 催化从各种炔丙基醚衍生物生成不饱和卡宾配合物中间体。这些原位生成的不饱和卡宾配合物与各种乙烯基醚发生 [3+2] 环加成反应，从而以高产率有效形成与五元环稠合的吲哚、萘酚和苯并呋喃。
• Construction of Cyclohepta[b]indoles via Platinum-Catalyzed Intermolecular Formal [4+3]-Cycloaddition Reaction of α,β-Unsaturated Carbene Complex Intermediates with Siloxydienes
  作者：Nobuharu Iwasawa、Hiroyuki Kusama、Hideyuki Sogo、Kodai Saito、Takuya Suga

  DOI：10.1055/s-0033-1338938

  日期：——

  Platinum(II)-catalyzed intermolecular formal [4+3]-cycloaddition reaction of α,β-unsaturated carbene complex intermediates with siloxydienes proceeded under mild conditions to give cyclohepta[b]indole derivatives in good yield. The reaction was found to proceed via 1,2-alkyl shift of the carbene complex intermediates obtained by [4+2]-cycloaddition reaction of the unsaturated carbenes with dienes.

  铂 (II) 催化的 α,β-不饱和卡宾配合物中间体与甲硅烷氧基二烯的分子间形式 [4+3]-环加成反应在温和条件下进行，以良好的收率得到环庚 [b] 吲哚衍生物。发现该反应通过不饱和卡宾与二烯的 [4+2]-环加成反应获得的卡宾配合物中间体的 1,2-烷基转移进行。
• Synthesis of diindolylmethanes and indolo[3,2-b]carbazoles, compounds formed thereby, and pharmaceutical compositions containing them
  申请人：Wisconsin Alumni Research Foundation

  公开号：US10730833B2

  公开（公告）日：2020-08-04

  Described is a method to make diindolylmethanes and indolyl/pyrrolylmethanes, The method includes the steps of contacting an ether comprising an arylpropargyl moiety and an amine-protected, substituted or unsubstituted aniline moiety with a substituted or unsubstituted indol or a substituted or unsubstituted pyrrole, in the presence of a metal-containing catalyst, for a time and at a temperature to cause an annulation/arylation cascade reaction that yields a diindolylmethane or a indolyl/pyrrolylmethane. The resulting compounds are effective to modulate activity of arylhydrocarbon receptors, to inhibit activity of PCSK9, and to stimulate secretion of glucagon-like peptide 1 in mammals.

  描述了一种制造二吲哚甲烷和吲哚基/吡咯基甲烷的方法，该方法包括以下步骤：将包含芳基丙炔基和胺保护的取代或未取代的苯胺基的醚与取代或未取代的吲哚或取代或未取代的吡咯接触、在含金属催化剂存在下，在一定时间和温度下进行环化/芳基化级联反应，生成二吲哚基甲烷或吲哚基/吡咯基甲烷。所得化合物可有效调节芳基烃受体的活性，抑制 PCSK9 的活性，并刺激哺乳动物分泌胰高血糖素样肽 1。
• Photoprotective compositions containing Malassezia-derived compounds and/or chemical analogs thereof
  申请人：Versicolor Technologies, LLC

  公开号：US11220491B2

  公开（公告）日：2022-01-11

  The present invention relates to compounds, compositions, and methods for modulating skin pigmentation and treating or preventing UV-induced skin damage, erythema, aging of the skin, sunburn, and hyperpigmentation in a subject. The compounds, compositions, and methods of the present invention generally involve Malassezia-derived compounds, including malassezin and indirubin, and/or chemical analogs thereof. Other applications of the compounds and compositions disclosed herein include, but are not limited to, improving hyperpigmentation caused by a hyperpigmentation disorder, inducing melanocyte apoptosis, and modulating arylhydrocarbon receptor (AhR) activity, melanogenesis, melanin production, melanosome biogenesis, melanosome transfer, melanocyte activity, and melanin concentration.

  本发明涉及调节皮肤色素沉着和治疗或预防紫外线引起的皮肤损伤、红斑、皮肤老化、晒伤和受试者色素沉着的化合物、组合物和方法。本发明的化合物、组合物和方法通常涉及马拉色菌衍生的化合物，包括马拉色素和靛玉红，和/或其化学类似物。本文公开的化合物和组合物的其他应用包括但不限于改善色素沉着症引起的色素沉着，诱导黑色素细胞凋亡，调节芳基烃受体（AhR）活性、黑色素生成、黑色素生成、黑色素小体生物生成、黑色素小体转移、黑色素细胞活性和黑色素浓度。